CN107556326A - A kind of sulfur heterocyclic ring derivative and its organic luminescent device - Google Patents
A kind of sulfur heterocyclic ring derivative and its organic luminescent device Download PDFInfo
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- CN107556326A CN107556326A CN201710957167.0A CN201710957167A CN107556326A CN 107556326 A CN107556326 A CN 107556326A CN 201710957167 A CN201710957167 A CN 201710957167A CN 107556326 A CN107556326 A CN 107556326A
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Abstract
The invention discloses a kind of sulfur heterocyclic ring derivative and its organic luminescent device, it is related to organic optoelectronic materials technology.The present invention is with spiral shell [cyclopenta [1,2 b:4,3 b'] Dithiophene 7,9' thioxanthenes] 10', 10' dioxide is agent structure, because element sulphur has stronger short of electricity sub-feature, sulphur sulfone group has good electron injection and transmission characteristic, the triplet singlet level for reducing molecule by rationally designing is poor, reasonable adjusting molecular entergy level, synthesizing new sulfur-bearing luminous organic material, can effectively improve device light emitting efficiency, have cut-in voltage low, the advantages that photochromic stability is good, long lifespan, also there is high luminous efficiency in the case where startup voltage is relatively low.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to a kind of sulfur heterocyclic ring derivative and its organic light emission
Device.
Background technology
At present, the research of electroluminescent organic material is carried out extensively in academia and industrial quarters, almost all of to know
Name electronics corporation and chemical company all puts into huge fund and manpower enters this field, the organic electroluminescence of a large amount of function admirables
Luminescent material is developed successively.But the technological industrialization process still faces many key issues, it is necessary to design new property
Preferably material it can be adjusted.
The luminous injection type that belongs to of organic electroluminescence device lights.Under forward voltage driving, anode is noted to luminescent layer
Enter hole, negative electrode injects electronics to luminescent layer.Injected holes and electronics meet in luminescent layer is combined into exciton, and exciton is compound
And luminescent material is transferred energy to, the latter lights by radiative relaxation process.Compared with inorganic light-emitting diode, You Jifa
The driving voltage of optical device is higher, and luminosity is relatively low and efficiency has much room for improvement.Element sulphur has stronger short of electricity sub-feature, sulphur
Sulfone group has good electron injection and transmission characteristic, and the electroluminescent organic material based on sulfur-bearing also went out successively in recent years
It is existing, but optimize general lack of MOLECULE DESIGN, cause device cut-in voltage high, the defects of short life.The present invention is namely based on this side
The application in face and design and synthesize new material system and it is realized into application in the devices.
The content of the invention
It is an object of the invention to provide a kind of sulfur heterocyclic ring derivative and its organic luminescent device.Sulfur heterocyclic ring provided by the invention
Derivative glass transition temperature is high, thermal stability is high, preparation method is simple, is used the derivative as the material of main part in luminescent layer
And manufactured organic luminescent device, the advantages of driving voltage is low, luminous efficiency is high is shown, is the luminous organic material of function admirable.
The invention provides a kind of sulfur heterocyclic ring derivative, its general formula of molecular structure such as following formula (I) are shown：
Wherein：R1~R2Can independently selected from hydrogen atom, cyano group, substituted or unsubstituted C1~C20 alkyl, substitution or
Unsubstituted C1~C10 alkoxy, substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring
Base or substituted or unsubstituted C5~C60 heterocyclic radicals.
Preferably, R1、R2Independent is selected from substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C10~C30
Condensed ring radical or substituted or unsubstituted C5~C30 heterocyclic radicals.
Preferably, R1、R2It is independent not take selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substitution or
The anthryl in generation, substituted or unsubstituted pyrenyl, substituted or unsubstituted Sanya phenyl, substituted or unsubstituted fluorenyl, substitution or
Unsubstituted carbazyl, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophenes base, substitution or not
One kind in substituted benzo pyrimidine radicals, substituted or unsubstituted benzo pyridine radicals.
Preferably, any one of sulfur heterocyclic ring derivative provided by the present invention in chemical constitution as follows：
。
Present invention also offers a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode
Between one or more organic compound layers, it is at least one layer of in the organic compound layer to include at least one described sulfur-bearing
Hete rocyclic derivatives.
Preferably, the organic compound layer includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, sky
At least one layer in cave barrier layer, electron transfer layer, electron injecting layer.
Preferably, described sulfur heterocyclic ring derivative is used as luminescent layer material of main part in organic electroluminescence device.
Beneficial effects of the present invention：
Sulfur heterocyclic ring derivative provided by the present invention, with spiral shell [cyclopenta [1,2-b:4,3-b'] Dithiophene -7,
9'- thioxanthenes] 10', 10'- dioxide is agent structure, and because element sulphur has stronger short of electricity sub-feature, sulphur sulfone group has good
Good electron injection and transmission characteristic, reasonable adjusting molecule energy poor by the triplet singlet level for rationally designing reduction molecule
Level, the sulfur-bearing luminous organic material that synthesizing new glass transition temperature is high, thermal stability is high, can effectively improve device light emitting efficiency, have
There is the advantages that cut-in voltage is low, and photochromic stability is good, long lifespan, also there is high luminous efficiency in the case where startup voltage is relatively low.
Embodiment
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, art technology
The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to protection scope of the present invention.
The invention provides a kind of sulfur heterocyclic ring derivative, its general formula of molecular structure such as following formula (I) are shown：
Wherein：R1~R2Can independently selected from hydrogen atom, cyano group, substituted or unsubstituted C1~C20 alkyl, substitution or
Unsubstituted C1~C10 alkoxy, substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring
Base or substituted or unsubstituted C5~C60 heterocyclic radicals.
Preferably, R1、R2Independent is selected from substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C10~C30
Condensed ring radical or substituted or unsubstituted C5~C30 heterocyclic radicals.
Preferably, R1、R2It is independent not take selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substitution or
The anthryl in generation, substituted or unsubstituted pyrenyl, substituted or unsubstituted Sanya phenyl, substituted or unsubstituted fluorenyl, substitution or
Unsubstituted carbazyl, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophenes base, substitution or not
One kind in substituted benzo pyrimidine radicals, substituted or unsubstituted benzo pyridine radicals.
Preferably, any one of sulfur heterocyclic ring derivative of the present invention in chemical constitution as follows：
。
Some specific structure types of sulfur heterocyclic ring derivative of the present invention are enumerated above, but it is of the present invention
Sulfur heterocyclic ring derivative is not limited to these listed chemical constitutions, based on every (I) by formula, R1、R2To be as defined above
Group should all be included.
Sulfur heterocyclic ring derivative of the present invention, it can be prepared by following route：
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, with well known to those skilled in the art such
The normal condition of reaction.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, can
Think commercially available prod or be prepared using preparation method well-known to those skilled in the art.Wherein, the R1、R2Selection
It is same as above, it will not be repeated here.
The present invention also provides a kind of organic luminescent device.What the organic luminescent device was well known to those skilled in the art
Organic luminescent device, organic luminescent device of the present invention include first electrode, second electrode and are placed in two electrode
Between one or more organic compound layers.It is at least one layer of in the organic compound layer to spread out comprising at least one sulfur heterocyclic ring
The Blue-light emitting host material of biology.The organic compound layer includes hole injection layer, hole transmission layer, electronic barrier layer, luminous
At least one layer in layer, hole blocking layer, electron transfer layer, electron injecting layer.It is preferred that the sulfur heterocyclic ring derivative is organic
It is used as luminescent layer material of main part in luminescent device.
Embodiment 1：The synthesis of compound 12
Step1. thioxanthene-9-one (30mmol), 150ml acetic acid, 30ml H are added in 250ml flasks2O2(35%) exist
Reaction 6 hours under 120 degree, reaction are cooled to room temperature after terminating, add 200ml water, separate out white solid and filter, after filtering
White solid is washed after being dissolved in dichloromethane, with being spin-dried for obtaining white powder product A, yield after anhydrous sodium sulfate drying
94%.
Step2. thienyl carbazole boric acid (5.6mmol), adjacent bromine iodothiophen are sequentially added in 250ml flasks
(7.0mmol), 40ml toluene, 20ml ethanol and 20ml 2M solution of potassium carbonate, it is eventually adding four (triphenylphosphines) and closes palladium
(0.3mmol), the lower reaction of 100 degree of nitrogen protection 12 hours, is cooled to room temperature, is extracted with dichloromethane, washs and with anhydrous sulphur
Sour magnesium is dried, and is evaporated under reduced pressure after removing solvent, is that solvent column chromatography obtains yellow solid 12-B using dichloromethane petroleum ether,
Yield 76%.
Step3. compound 12-B (6.3mmol) prepared by previous step is added in 250ml flasks, it is anhydrous to add 80ml
Dry tetrahydrofuran, be cooled to -78 degree, 2.5M n-BuLis (7mmol) are slowly added dropwise, after completion of dropwise addition again -78 degree under it is anti-
Answer 2 hours, then 20ml compounds A tetrahydrofuran solution is slowly dropped in reaction flask, it is small that 24 are reacted at room temperature after dropwise addition
When, reaction adds 100ml saturated sodium bicarbonate solutions after terminating and reaction is quenched.Extracted with dichloromethane, anhydrous sodium sulfate drying
Dry dissolving is rotated afterwards obtains solid.60ml acetic acid and 5ml concentrated hydrochloric acids are directly added into, 120 degree back flow reaction 8 hours, reaction are tied down
Room temperature is cooled to after beam, adds 200ml water, washes out solid.Solid is dissolved in dichloromethane after suction filtration, after washing revolving is dried, profit
It is that solvent column chromatography obtains target compound 12, yield 55% with dichloromethane petroleum ether.
Mass spectrum m/z：557.08 (calculated values：557.06).Theoretical elemental content (%) C33H19NO2S3：C, 71.07；H,
3.43；N, 2.51；O, 5.74；S, 17.25.Survey constituent content (%)：C, 71.07；H, 3.43；N, 2.51；O, 5.74；S,
17.25.The above results confirm that it is target product to obtain product.
Embodiment 2：The synthesis of compound 26
Step1. with embodiment 1.
Step2. phenyl carbazole boric acid (14.5mmol), adjacent bromine thiophene biniodide are sequentially added in 250ml flasks
(7.0mmol), 60ml toluene, 20ml ethanol and 20ml 2M solution of potassium carbonate, it is eventually adding four (triphenylphosphines) and closes palladium
(0.7mmol), the lower reaction of 100 degree of nitrogen protection 24 hours, is cooled to room temperature, is extracted with dichloromethane, washs and with anhydrous sulphur
Sour magnesium is dried, and is evaporated under reduced pressure after removing solvent, is that solvent column chromatography obtains yellow solid 26-B using dichloromethane petroleum ether,
Yield 36%.
Step3. compound 26-B (5.5mmol) prepared by previous step is added in 250ml flasks, it is anhydrous to add 80ml
Dry tetrahydrofuran, be cooled to -78 degree, 2.5M n-BuLis (8mmol) are slowly added dropwise, after completion of dropwise addition again -78 degree under it is anti-
Answer 2 hours, then 150ml compounds A tetrahydrofuran solution is slowly dropped in reaction flask, it is small that 24 are reacted at room temperature after dropwise addition
When, reaction adds 100ml saturated sodium bicarbonate solutions after terminating and reaction is quenched.Extracted with dichloromethane, anhydrous sodium sulfate drying
Dry dissolving is rotated afterwards obtains solid.60ml acetic acid and 5ml concentrated hydrochloric acids are directly added into, 120 degree back flow reaction 8 hours, reaction are tied down
Room temperature is cooled to after beam, adds 200ml water, washes out solid.Solid is dissolved in dichloromethane after suction filtration, after washing revolving is dried, profit
It is that solvent column chromatography obtains target compound 26, yield 35% with dichloromethane petroleum ether.
Mass spectrum m/z：804.8 (calculated values：804.5).Theoretical elemental content (%) C49H28N2O2S4：C, 73.11；H,
3.51；N, 3.48；O, 3.97；S, 15.93.Survey constituent content (%)：C, 73.11；H, 3.52；N, 3.48；O, 3.97；S,
15.93.The above results confirm that it is target product to obtain product.
Embodiment 3：The synthesis of compound 16
Step1. with embodiment 1.
Step2. thienyl triphenylamine boric acid (12.5mmol), adjacent bromine iodothiophen are sequentially added in 250ml flasks
(5.8mmol), 60ml toluene, 20ml ethanol and 20ml2M solution of potassium carbonate, it is eventually adding four (triphenylphosphines) and closes palladium
(0.66mmol), the lower reaction of 100 degree of nitrogen protection 24 hours, is cooled to room temperature, is extracted with dichloromethane, washs and with anhydrous sulphur
Sour magnesium is dried, and is evaporated under reduced pressure after removing solvent, is that solvent column chromatography obtains yellow solid 16-B using dichloromethane petroleum ether,
Yield 42%.
Step3. in 250ml flasks add previous step prepare compound 16-B (7.0mmol), add 100ml without
Water dry tetrahydrofuran, be cooled to -78 degree, 2.5M n-BuLis (10mmol) are slowly added dropwise, after completion of dropwise addition again -78 degree under
Reaction 2 hours, then 130ml compounds A tetrahydrofuran solution is slowly dropped in reaction flask, 24 are reacted at room temperature after dropwise addition
Hour, reaction adds 100ml saturated sodium bicarbonate solutions after terminating and reaction is quenched.Extracted with dichloromethane, anhydrous sodium sulfate is done
The dry dissolving of revolving obtains solid after dry.60ml acetic acid and 5ml concentrated hydrochloric acids are directly added into, 120 degree are descended back flow reaction 8 hours, reaction
Room temperature is cooled to after end, adds 200ml water, washes out solid.Solid is dissolved in dichloromethane after suction filtration, after washing revolving is dried,
It is that solvent column chromatography obtains target compound 16, yield 45% using dichloromethane petroleum ether.
Mass spectrum m/z：635.02 (calculated values：635.10).Theoretical elemental content (%) C39H25NO2S3：C, 73.67；H,
3.96；N, 2.20；O, 5.03；S, 15.13.Survey constituent content (%)：C, 73.67；H, 3.96；N, 2.20；O, 5.03；S,
15.13.The above results confirm that it is target product to obtain product.
Embodiment 4：The preparation of luminescent device 1
To compare luminescent properties of the compounds of this invention as OLED emitting layer material, the present embodiment uses multilayer
OLED structure prepares device.
Selection ito glass is anode, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 1 × 10-4Pa, above-mentioned
Vacuum evaporation MoO in anode grid substrate3For 8-10nm as hole injection layer, it is main body that 50nmCBP and target compound are deposited respectively
Luminescent layer, using FIrpic as doping object (6%).Evaporation PyPb40nm is electron transfer layer.Vacuum is steamed on the electron transport layer
LiF and Al layers are plated as negative electrode, thickness is respectively 1nm and 200nm.
Device performance see the table below in the present embodiment：
The electroluminescence characters of the organic luminescent device of table 1
| Emitting layer material | Voltage (V) | Brightness (cd/m2) | Efficiency (cd/A) |
| CBP | 3.1 | 12056 | 38.2 |
| Compound 12 | 2.9 | 20730 | 45.2 |
| Compound 26 | 2.6 | 19855 | 44.5 |
| Compound 16 | 3.3 | 20113 | 47.2 |
Result above shows, the application of novel sulfurized Hete rocyclic derivatives of the invention in an organic light emitting device, have compared with
High luminosity and luminous efficiency, its switching voltage also decrease, and are luminous organic materials of good performance.
Although the present invention is described in conjunction with the embodiments, the invention is not limited in above-described embodiment.It should refer to
Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field
Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (7)
1. a kind of sulfur heterocyclic ring derivative, it is characterised in that shown in its general formula of molecular structure such as following formula (I)：
Wherein：R1~R2It can not take independently selected from hydrogen atom, cyano group, substituted or unsubstituted C1~C20 alkyl, substitution or
C1~the C10 in generation alkoxy, substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring radicals or
Substituted or unsubstituted C5~C60 heterocyclic radicals.
A kind of 2. sulfur heterocyclic ring derivative according to claim 1, it is characterised in that R1、R2It is independent selected from substitution or not
Substituted C6~C30 aryl, substituted or unsubstituted C10~C30 condensed ring radicals or substituted or unsubstituted C5~C30 heterocyclic radicals.
A kind of 3. sulfur heterocyclic ring derivative according to claim 1, it is characterised in that R1、R2It is independent selected from substitution or not
Substituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substitution or not
Substituted Sanya phenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted dibenzo furan
Mutter base, substituted or unsubstituted dibenzothiophenes base, substituted or unsubstituted benzo pyrimidine radicals, substituted or unsubstituted benzo pyrrole
One kind in piperidinyl.
4. a kind of sulfur heterocyclic ring derivative according to claim 1, it is characterised in that in chemical constitution as follows
Any one：
。
5. a kind of organic luminescent device, including first electrode, second electrode and the one or more being placed between two electrode
Organic compound layer, it is characterised in that at least one layer of any one comprising at least one such as claim 1-4 in organic compound layer
Sulfur heterocyclic ring derivative described in.
6. organic luminescent device according to claim 5, it is characterised in that the organic compound layer injects comprising hole
At least one layer in layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer.
7. organic luminescent device according to claim 5, it is characterised in that the sulfur heterocyclic ring derivative is in organic light emission
It is used as luminescent layer material of main part in device.
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| CN106800567A (en) * | 2016-12-12 | 2017-06-06 | 中节能万润股份有限公司 | A kind of acridine spiral shell thioxanthene sulfone derivatives and its preparation method and application |
| CN106800559A (en) * | 2016-12-29 | 2017-06-06 | 中节能万润股份有限公司 | A kind of thioxanthene class electroluminescent organic material and its preparation method and application |
-
2017
- 2017-10-16 CN CN201710957167.0A patent/CN107556326A/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015197156A1 (en) * | 2014-06-25 | 2015-12-30 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN106459749A (en) * | 2014-07-01 | 2017-02-22 | 碧山油漆股份公司 | Compound for phosphorescent host and organic light-emitting element comprising same |
| CN104761547A (en) * | 2015-03-26 | 2015-07-08 | 深圳市华星光电技术有限公司 | Thioxanthone-aromatic amine compound and organic light-emitting device using same |
| CN106800567A (en) * | 2016-12-12 | 2017-06-06 | 中节能万润股份有限公司 | A kind of acridine spiral shell thioxanthene sulfone derivatives and its preparation method and application |
| CN106699742A (en) * | 2016-12-29 | 2017-05-24 | 中节能万润股份有限公司 | Thiaxanthene dioxide type organic electroluminescence material and preparation method and application thereof |
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Application publication date: 20180109 |