CN109942578A - Miscellaneous anthracene class organic compound and its preparation method and application - Google Patents
Miscellaneous anthracene class organic compound and its preparation method and application Download PDFInfo
- Publication number
- CN109942578A CN109942578A CN201910323721.9A CN201910323721A CN109942578A CN 109942578 A CN109942578 A CN 109942578A CN 201910323721 A CN201910323721 A CN 201910323721A CN 109942578 A CN109942578 A CN 109942578A
- Authority
- CN
- China
- Prior art keywords
- substituted
- added
- organic compound
- reaction
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to technical field of semiconductors, and in particular to a kind of miscellaneous anthracene class organic compound and its preparation method and application.The miscellaneous anthracene class organic compound structure formula is as described in chemical formula 1:
Description
Technical field
The present invention relates to technical field of semiconductors, and in particular to a kind of miscellaneous anthracene class organic compound and preparation method thereof and answers
With.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.OLED luminescent device includes electrode material and the organic functional material that is clipped between Different electrodes, respectively
Kind different function material is overlapped mutually depending on the application collectively constitutes OLED luminescent device together.It is electric when applying to its two end electrodes
When pressing, and passing through the positive and negative charge in electric field action organic functional material layer, positive and negative charge is further compound in luminescent layer, i.e.,
Generate OLED electroluminescent.
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, applies in industry
OLED device structure then includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron-transport
A variety of film layers such as layer, electron injecting layer, that is to say, that the photoelectric functional material applied to OLED device is injected including at least hole
Material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form have rich and various
The characteristics of property.In addition, used photoelectric functional material has stronger choosing for the collocation of the OLED device of different structure
Selecting property, performance of the identical material in different structure device may also be completely totally different.Therefore new structural function is developed
Energy material just seems most important.
Summary of the invention
The object of the present invention is to provide a kind of novel miscellaneous anthracene class organic compound and its preparation method and application, the present invention
Compound glass transition temperature with higher and molecule thermal stability, are optimized by device architecture, can effectively promote OLED device
Photoelectric properties and device service life.
To achieve the goals above, technical solution of the present invention is specific as follows:
A kind of miscellaneous anthracene class organic compound, structural formula as described in chemical formula 1:
Wherein:
R1And R2Each independently represent the alkyl for substituted or non-substituted C1~C60, the naphthenic base of C3~C60, substitution
Or the alkenyl of non-substituted C2~C60, the cycloalkenyl of C3~C60, the alkynyl of substituted or non-substituted C3~C60, C3~C60
The heterocycle of cycloalkynyl radical, the aryl of substituted or non-substituted C6~C60 or C6~C60；
R3And R4It each independently represents: hydrogen, the isotope of hydrogen, halogen, cyano, nitro, hydroxyl, amino, sulfonic group, sulphur
Acyl group, phosphate, phosphoryl, substituted or non-substituted silicon substrate, boryl, phosphorus base, substituted or non-substituted C1~C60 alkane
Base, the naphthenic base of C3~C60, alkoxy, alkylamino radical, alkane sulfydryl, the alkenyl of substituted or non-substituted C2~C60, C3~C60
Cycloalkenyl, the alkynyl of substituted or non-substituted C3~C60, the cycloalkynyl radical of C3~C60, substituted or non-substituted C6~C60 aryl
Or the heterocycle of C6~C60；Or it is connect with adjacent substituents and to form the monocycle for being substituted or being unsubstituted or polycyclic C3-C30
Aliphatic ring or aromatic ring, carbon atom it is replaceable at least one be selected from nitrogen, oxygen or sulphur hetero atom；
M, n is 0~4 integer；
Ar1For the aromatic ring or substitution of substitution or unsubstituted C5-C30 or the heterocycle of unsubstituted C5~C60；
Ar2For the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 aryl or substitution or not
The heteroaryl of substituted C1~C30；Or the aliphatic ring or fragrance to form monocycle or polycyclic C3-C30 are connect with adjacent substituents
Race's ring, the replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of carbon atom.
In the above-mentioned technical solutions, preferably Ar1For phenyl ring, naphthalene nucleus, anthracene nucleus, pyrene ring or phenanthrene ring.
In the above-mentioned technical solutions, preferably Ar2For phenyl, dibiphenylyl, terphenyl, naphthalene, anthryl, phenanthryl, pyrenyl,
Furyl, thienyl, pyridyl group, pyrimidine radicals, pyridazinyl, pyrazinyl, triazine radical, quinazoline, benzimidazole, acridine and its derivative
One of object, oxazole, thiazole, phenthazine, isopropyl and cyclohexyl.
In the above-mentioned technical solutions, further preferred Ar2For any one in following structures:
Wherein: R be hydrogen, halogen, cyano, the alkyl of C1~C30, the aryl of C6~C50, the aralkyl of C7~C50, C7~
Alkoxy aryl, the aryl alkane sulfydryl of C7~C50 or the heteroaryl of C5~C50 of C50；And described-R indicates benzene where it
Any position of ring, " * " are link position.
In the above-mentioned technical solutions, the miscellaneous anthracene class organic compound is selected from any one in flowering structure:
A kind of preparation method of miscellaneous anthracene class organic compound, comprising the following steps:
1. the synthesis of intermediate C: under nitrogen atmosphere, raw material B and NaOt-Bu are added in dry toluene and stir 20min,
Raw material A, Pd (OAc) is then added2With P (t-Bu)3, reacted after heating；Monitoring after reaction, is cooled to room temperature, is added
Water washing, layering, extraction, silica gel column chromatography post separation obtain intermediate C；Preferable reaction temperature is 80 DEG C, reaction time 6h；
2. the synthesis of intermediate E: intermediate C being dissolved in anhydrous tetrahydro furan, is cooled to 0 DEG C or so, format examination is added dropwise
Agent D, then heating is reacted；After reaction, it is cooled to room temperature, water washing, layering is added, makes to be extracted with ethyl acetate,
Gained organic phase is washed with saturated sodium bicarbonate aqueous solution, and silica gel column chromatography post separation after drying obtains intermediate E；It is preferred that reacting
Temperature is 40 DEG C, reaction time 6h；
When raw material B is to contain R1When group, the grignard reagent D is R2MgBr；When raw material B is to contain R2It is described when group
Grignard reagent D is R1MgBr；
3. the synthesis of intermediate F: intermediate E being dissolved in dry tetrahydrofuran and toluene Mixed Solvent, added under room temperature
Enter methanesulfonic acid, is reacted；After reaction, it is separately added into water and ethyl acetate stirring, organic phase, saturated carbon are collected in layering
Sour hydrogen sodium water solution washing, removes organic solvent after dry, obtains intermediate F；Preferred reaction time is 8h；
4. the synthesis of intermediate H: under nitrogen atmosphere, intermediate F and NaOt-Bu, which are added in dry toluene, stirs 20min,
Intermediate G, Pd (OAc) then is added2With P (t-Bu)3, reacted after heating；Monitoring after reaction, is cooled to room temperature, adds
Enter water washing, layering, extraction, silica gel column chromatography post separation obtains intermediate H；Preferable reaction temperature is 80 DEG C, and the reaction time is
6h；
5. the synthesis of intermediate compound I: intermediate H being added in triethyl phosphite, will be reacted after reaction heating；Instead
It should finish, be cooled to room temperature, reaction solution is slowly added into ice water, have and measure solid precipitation greatly, stir 1h, filtering, solid
Middle addition methylene chloride, stirring solid dissolve substantially, and petroleum ether, which is added, solid precipitation, stirs 1h, and filtering drying obtains centre
Body I；Preferable reaction temperature is 155 DEG C, and the reaction time is 5 hours；
6. the synthesis of finished product shown in chemical formula 1: under nitrogen atmosphere, intermediate compound I and NaOt-Bu being added to dry toluene
Then intermediate J, Pd (OAc) is added in middle stirring 20min2With P (t-Bu)3, reacted after heating；It monitors after reaction,
It is cooled to room temperature, water washing, layering, extraction is added, silica gel column chromatography post separation obtains finished product shown in chemical formula 1；It is preferred that anti-
Answering temperature is 80 DEG C, reaction time 6h；
Its synthetic route is as follows:
Wherein: R1、R2、R3、R4、Ar1、Ar2, the range that limits in m and n and chemical formula 1 it is consistent, X is halogen.
The present invention also provides the applications that a kind of miscellaneous anthracene class organic compound is used to prepare organic electroluminescence device.Institute
Stating organic electroluminescence device includes that at least one layer of functional layer contains the organic compound that the chemical formula 1 indicates.
The present invention also provides a kind of organic electroluminescence device, including electronic barrier layer, the electronic blocking layer material
The organic compound indicated for the chemical formula 1.
The present invention also provides a kind of organic electroluminescence device, including luminescent layer, the luminescent layer contains the change
The organic compound that formula 1 indicates.
The beneficial effects of the present invention are:
Miscellaneous anthracene class organic compound provided by the invention, can be applied to OLED luminescent device production, and with device ratio
It is compared compared with example 1, either efficiency or service life obtains larger change than known OLED material, and the service life of especially device declines
Subtract and obtains biggish promotion.
Preparation method is simple for miscellaneous anthracene class organic compound provided by the invention, and yield is high, is suitable for industrialized production.
Specific embodiment
Embodiment 1: the synthesis of compound 1
Under nitrogen atmosphere, 2- aminobenzophenone (19.7g, 100mmol) and NaOt-Bu (19.2g, 200mmol) are added
Enter into 200mL dry toluene and stir 20min, bromobenzene (15.6g, 100mmol), Pd (OAc) is then added2(0.2g, 1mmol)
With P (t-Bu)3(0.8g, 2mmol) is warming up to 80 DEG C of reaction 6h.Monitoring after reaction, is cooled to room temperature, and 300mL water is added
Washing, layering, extraction, silica gel column chromatography post separation obtain compound C-124.58g, yield 90%.
Intermediate C-1 (24.58g, 90mmol) is dissolved in 300mL anhydrous tetrahydro furan, is cooled to 0 DEG C or so, is added dropwise
Phenylmagnesium bromide solution (44mL, 110mmol) then rises to 40 DEG C of reaction 6h.After reaction, it is cooled to room temperature, is added
300mL water washing, layering, the extraction of 300mL ethyl acetate, gained organic phase is washed with saturated sodium bicarbonate aqueous solution, after dry
Silica gel column chromatography post separation obtains intermediate E -125.28g, yield 80%.
Intermediate E -1 (25.28g, 72mmol) is dissolved in dry 150mL tetrahydrofuran and 150mL toluene Mixed Solvent
In, methanesulfonic acid (34.56g, 360mmol) is added under room temperature, reacts 8h.After reaction, 300mL water and acetic acid second are separately added into
Organic phase is collected in ester stirring, layering, and saturated sodium bicarbonate aqueous solution washing removes organic solvent after dry, obtains intermediate F-
122.79g yield 95%.
Under nitrogen atmosphere, intermediate F-1 (22.79g, 72mmol) and NaOt-Bu (13.8g, 144mmol) are added to
20min is stirred in 200mL dry toluene, intermediate G-1 (14.47g, 72mmol), Pd (OAc) is then added2(0.14g,
0.72mmol) and P (t-Bu)3(0.58g, 1.44mmol) is warming up to 80 DEG C of reaction 6h.Monitoring after reaction, is cooled to room
Temperature, is added 300mL water washing, layering, extraction, and silica gel column chromatography post separation obtains intermediate H-127.8g, yield 85%.
Intermediate H-1 (27.8g 61.2mmol) is added in 140mL triethyl phosphite, and reaction is heated to 155 DEG C,
Reaction 5 hours.End of reaction is cooled to room temperature.Reaction solution is slowly added into 1L ice water, has and measures solid precipitation greatly, stir
1h to be mixed, is filtered, methylene chloride 100mL is added in solid, stirring solid dissolves substantially, and 500mL petroleum ether, which is added, solid precipitation,
Stir 1h, filtering drying.Obtain intermediate compound I -119.38g, yield 75%.
Under nitrogen atmosphere, intermediate compound I -1 (19.38g, 45.9mmol) and NaOt-Bu (8.8g, 91.8mmol) are added to
20min is stirred in 200mL dry toluene, and bromobenzene (7.16g, 45.9mmol), Pd (OAc) is then added2(0.092g,
0.46mmol) and P (t-Bu)3(0.368g, 0.92mmol) is warming up to 80 DEG C of reaction 6h.Monitoring after reaction, is cooled to room
Temperature, is added 300mL water washing, layering, extraction, and silica gel column chromatography post separation obtains compound 118 .75g, yield 82%.ESI-MS
(m/z) (M+): theoretical value 498.21, measured value 498.34.
Embodiment 2: the synthesis of compound 2
According to the method prepare compound 2 of compound 1 in embodiment 1.The difference is that by the intermediate in embodiment 1
J-1 is changed to intermediate J-2 (four bromo biphenyls), remaining is identical, obtains compound 2, yield 78%.ESI-MS (m/z) (M+): theoretical
Value is 574.24, measured value 574.54.
Embodiment 3: the synthesis of compound 10
According to the method prepare compound 10 of compound 1 in embodiment 1.The difference is that by the centre in embodiment 1
Body J-1 is changed to intermediate J-10 (bromo- 9 phenyl carbazole of 3-), remaining is identical, obtains compound 10, yield 80%.ESI-MS(m/
Z) (M+): theoretical value 663.27, measured value 663.74.
Embodiment 4: the synthesis of compound 14
According to the method prepare compound 14 of compound 1 in embodiment 1.The difference is that by raw material B-1 in embodiment 1
It is changed to raw material B-14, grignard reagent D-1 is changed to D-14, remaining is identical, obtains compound 14, yield 75%.ESI-MS(m/z)(M
+): theoretical value 506.24, measured value 506.34.
Embodiment 5: the synthesis of compound 18
According to the method prepare compound 18 of compound 1 in embodiment 1.The difference is that by the centre in embodiment 1
Body J-1 is changed to intermediate J-18, remaining is identical.Obtain 18 yield 83%ESI-MS (m/z) (M+) of compound: theoretical value is
690.28 measured value 690.24.
Embodiment 6: the synthesis of compound 32
According to the method prepare compound 32 of compound 1 in embodiment 1.The difference is that by the raw material in embodiment 1
B-1 is changed to B-32, and J-1 is changed to intermediate J-32, remaining is identical, obtains compound 32, yield 76%.ESI-MS (m/z) (M+):
Theoretical value is 672.26, measured value 672.28.
Embodiment 7: the synthesis of compound 49
According to the method prepare compound 49 of compound 32 in embodiment 6.The difference is that by the centre in embodiment 6
Body J-32 is changed to J-49, remaining is identical, obtains compound 49, yield 79%.ESI-MS (m/z) (M+): theoretical value 638.24,
Measured value is 638.58.
Embodiment 8: the synthesis of compound 54
According to the method prepare compound 54 of compound 32 in embodiment 6.The difference is that by the centre in embodiment 6
Body J-32 is changed to J-54, remaining is identical, obtains compound 54, yield 81%.ESI-MS (m/z) (M+): theoretical value 625.25,
Measured value is 625.36.
Embodiment 9: the synthesis of compound 70
According to the method prepare compound 70 of compound 32 in embodiment 6.The difference is that by the centre in embodiment 6
Body J-32 is changed to J-70, remaining is identical.70 yield 79%ESI-MS (m/z) (M+) of compound: theoretical value 740.29 is obtained, it is real
Measured value is 740.86.
Embodiment 10: the synthesis of compound 72
According to the method prepare compound 72 of compound 32 in embodiment 6.The difference is that by the centre in embodiment 6
Body J-32 is changed to J-72, remaining is identical, obtains compound 72, yield 84%.ESI-MS (m/z) (M+): theoretical value 755.33,
Measured value is 755.36.
Embodiment 11: the synthesis of compound 84
According to the method prepare compound 84 of compound 1 in embodiment 1.The difference is that by the raw material in embodiment 1
B-1 is changed to B-84, and J-1 is changed to intermediate J-84, remaining is identical, obtains compound 84, yield 74%.ESI-MS (m/z) (M+):
Theoretical value is 878.34, measured value 878.18.
Embodiment 12: the synthesis of compound 90
According to the method prepare compound 90 of compound 1 in embodiment 1.The difference is that by the raw material in embodiment 1
B-1 is changed to B-90, and grignard reagent D-1 is changed to raw material D-84, remaining is identical, obtains compound 90, yield 84%.ESI-MS(m/
Z) (M+): theoretical value 664.29, measured value 664.78.
Embodiment 13: the synthesis of compound 92
According to the method prepare compound 92 of compound 1 in embodiment 1.The difference is that by the raw material in embodiment 1
B-1 is changed to B-92, and intermediate G-1 is changed to raw material G-92, and intermediate J-1 is changed to J-92, and remaining is identical.Obtain 92 yield of compound
81%ESI-MS (m/z) (M+): theoretical value 748.29, measured value 748.79.
With the heat point of compound and well known host compound CBP that thermogravimetry measurement embodiment 1~13 synthesizes
It solves temperature (Td).Using the glass transition temperature (Tg) of differential scanning calorimetry measurement above compound.As a result such as 1 institute of table
Show:
Table 1
| Compound | Td(℃) | Tg(℃) |
| 1 | 433 | 142 |
| 2 | 421 | 145 |
| 10 | 419 | 150 |
| 14 | 427 | 146 |
| 18 | 419 | 151 |
| 32 | 426 | 147 |
| 49 | 440 | 144 |
| 54 | 438 | 152 |
| 70 | 427 | 148 |
| 72 | 435 | 146 |
| 84 | 426 | 141 |
| 90 | 417 | 150 |
| 92 | 426 | 143 |
| CBP | 342 | 98 |
Device embodiments 1: a kind of electroluminescent device, preparation step include:
The ito anode layer on transparent substrate layer is cleaned, is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively,
Then it is handled 2 minutes in plasma cleaner；B) on ito anode layer, hole injection is deposited by vacuum evaporation mode
Layer material HAT-CN, with a thickness of 10nm, this layer is as hole injection layer；C) on hole injection layer, pass through vacuum evaporation mode
Hole mobile material NPB is deposited, with a thickness of 60nm, which is hole transmission layer；D) luminescent layer is deposited on hole transmission layer,
Use compound 1 in embodiment 1 as material of main part, Ir (ppy)3As dopant material, Ir (ppy)3With the matter of compound 1
Amount is than being 5:9:5, with a thickness of 30nm；F) on luminescent layer, electron transport material TPBI is deposited by vacuum evaporation mode, it is thick
Degree is 40nm；G) on electron transfer layer, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electron injecting layer；
H) on electron injecting layer, vacuum evaporation cathode Al (100nm), the layer is cathode reflection electrode layer, and the electroluminescent hair is made
Optical device.
Device embodiments 2: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 2.
Device embodiments 3: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 10.
Device embodiments 4: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 14.
Device embodiments 5: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 18.
Device embodiments 6: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 32.
Device embodiments 7: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 49.
Device embodiments 8: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 54.
Device embodiments 9: the present embodiment and device embodiments 1 the difference is that: the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 70.
Device embodiments 10: the present embodiment is with device embodiments 1 the difference is that the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 72.
Device embodiments 11: the present embodiment is with device embodiments 1 the difference is that the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 84.
Device embodiments 12: the present embodiment is with device embodiments 1 the difference is that the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 90.
Device embodiments 13: the present embodiment is with device embodiments 1 the difference is that the luminescent layer of electroluminescent device
Material of main part is the compounds of this invention 92.
Device comparative example 1: the present embodiment is with device embodiments 1 the difference is that the luminescent layer master of electroluminescent device
Body material is CBP.
The Electroluminescence Properties of the OLED of manufacture are shown in Table 2.
Table 2
| Compound | Current efficiency | Color | The LT95 service life | |
| Embodiment 1 | 1 | 1.8 | Green | 9.2 |
| Embodiment 2 | 2 | 2.0 | Green | 9.1 |
| Embodiment 3 | 10 | 1.9 | Green | 9.0 |
| Embodiment 4 | 14 | 2.3 | Green | 9.4 |
| Embodiment 5 | 18 | 2.1 | Green | 9.5 |
| Embodiment 6 | 32 | 2.5 | Green | 9.4 |
| Embodiment 7 | 49 | 2.4 | Green | 9.7 |
| Embodiment 8 | 54 | 1.9 | Green | 9.5 |
| Embodiment 9 | 70 | 2.1 | Green | 9.9 |
| Embodiment 10 | 72 | 2.4 | Green | 9.7 |
| Embodiment 11 | 84 | 2.6 | Green | 9.2 |
| Embodiment 12 | 90 | 2.4 | Green | 9.1 |
| Embodiment 13 | 92 | 2.2 | Green | 9.0 |
| Comparative example 1 | CBP | 1.0 | Green | 1.0 |
Device detection performance is reference with comparative example 1, and 1 device performance indexes of comparative example is set as 1.0.Comparative example 1
Current efficiency 28cd/A (@10mA/cm2)；LT95 life time decay is 2.5Hr under 5000 brightness.
It can be seen that organic compound of the present invention can be applied to the production of OLED luminescent device by the result in table, and
And compared with device comparative example 1, either efficiency or service life obtains larger change, especially device than known OLED material
The life time decay of part obtains biggish promotion.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of miscellaneous anthracene class organic compound, which is characterized in that its structural formula as described in chemical formula 1:
Wherein:
R1And R2Each independently represent the alkyl for substituted or non-substituted C1~C60, the naphthenic base of C3~C60, substitution or non-
The alkenyl of substituted C2~C60, the cycloalkenyl of C3~C60, the alkynyl of substituted or non-substituted C3~C60, C3~C60 cycloalkyne
The heterocycle of base, the aryl of substituted or non-substituted C6~C60 or C6~C60；
R3And R4Each independently represent: hydrogen, the isotope of hydrogen, halogen, cyano, nitro, hydroxyl, amino, sulfonic group, sulfonyl,
Phosphate, phosphoryl, substituted or non-substituted silicon substrate, boryl, phosphorus base, the alkyl of substituted or non-substituted C1~C60, C3~
The naphthenic base of C60, alkoxy, alkylamino radical, alkane sulfydryl, the alkenyl of substituted or non-substituted C2~C60, C3~C60 cycloalkenyl,
The alkynyl of substituted or non-substituted C3~C60, the cycloalkynyl radical of C3~C60, substituted or non-substituted C6~C60 aryl or C6~
The heterocycle of C60；Or it is connect with adjacent substituents and to form the alicyclic of the monocycle for being substituted or being unsubstituted or polycyclic C3-C30
Ring or aromatic ring, the replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of carbon atom；
M, n is 0~4 integer；
Ar1For the heterocycle of the aromatic ring or substituted or unsubstituted C5~C60 of substitution or unsubstituted C5-C30；
Ar2For the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 aryl or substituted or unsubstituted
C1~C30 heteroaryl；Or the aliphatic ring or aromatic ring to form monocycle or polycyclic C3-C30, carbon are connect with adjacent substituents
The replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of atom.
2. miscellaneous anthracene class organic compound according to claim 1, which is characterized in that Ar1For phenyl ring, naphthalene nucleus, anthracene nucleus, pyrene ring
Or phenanthrene ring.
3. miscellaneous anthracene class organic compound according to claim 1, which is characterized in that Ar2For phenyl, dibiphenylyl, terphenyl
Base, naphthalene, anthryl, phenanthryl, pyrenyl, furyl, thienyl, pyridyl group, pyrimidine radicals, pyridazinyl, pyrazinyl, triazine radical, quinoline azoles
One of quinoline, benzimidazole, acridine and its derivative, oxazole, thiazole, phenthazine, isopropyl and cyclohexyl.
4. miscellaneous anthracene class organic compound according to claim 1, which is characterized in that Ar2It is any in following structures
One:
Wherein: R is hydrogen, halogen, cyano, the alkyl of C1~C30, the aryl of C6~C50, the aralkyl of C7~C50, C7~C50
Alkoxy aryl, the aryl alkane sulfydryl of C7~C50 or the heteroaryl of C5~C50.
5. miscellaneous anthracene class organic compound according to claim 1, which is characterized in that it is selected from any one in flowering structure
Kind:
6. a kind of preparation method of miscellaneous anthracene class organic compound described in claim 1, which comprises the following steps:
1. the synthesis of intermediate C: under nitrogen atmosphere, raw material B and NaOt-Bu being added in toluene and stirred, raw material is then added
A、Pd(OAc)2With P (t-Bu)3, reacted after heating；Monitoring after reaction, is cooled to room temperature, be added water washing, layering,
Extraction, silica gel column chromatography post separation obtain intermediate C；
2. the synthesis of intermediate E: intermediate C being dissolved in anhydrous tetrahydro furan, grignard reagent D is added dropwise, then heating carries out anti-
It answers；After reaction, it is cooled to room temperature, water washing, layering is added, makes to be extracted with ethyl acetate, gained organic phase saturated carbon
Sour hydrogen sodium water solution washing, silica gel column chromatography post separation after drying obtain intermediate E；
3. the synthesis of intermediate F: intermediate E is dissolved in tetrahydrofuran and toluene Mixed Solvent, methanesulfonic acid is added under room temperature, into
Row reaction；After reaction, it is separately added into water and ethyl acetate stirring, organic phase, saturated sodium bicarbonate aqueous solution are collected in layering
Washing removes organic solvent after dry, obtains intermediate F；
4. the synthesis of intermediate H: under nitrogen atmosphere, intermediate F and NaOt-Bu, which are added in toluene, to be stirred, and is then added intermediate
Body G, Pd (OAc)2With P (t-Bu)3, reacted after heating；Monitoring after reaction, is cooled to room temperature, and water washing is added, divides
Layer, extraction, silica gel column chromatography post separation obtain intermediate H；
5. the synthesis of intermediate compound I: intermediate H being added in triethyl phosphite, will be reacted after reaction heating；It has reacted
Finish, be cooled to room temperature, reaction solution is added in ice water, there is a large amount of solid to be precipitated, stir, filter, dichloro is added in solid
Methane, stirring solid dissolution, petroleum ether, which is added, solid precipitation, stirs, and filters, and drying obtains intermediate compound I；
6. the synthesis of finished product shown in chemical formula 1: under nitrogen atmosphere, intermediate compound I and NaOt-Bu being added in dry toluene and stirred
It mixes, intermediate J, Pd (OAc) then is added2With P (t-Bu)3, reacted after heating；Monitoring after reaction, is cooled to room
Temperature, is added water washing, layering, extraction, and silica gel column chromatography post separation obtains finished product shown in chemical formula 1；
Its synthetic route is as follows:
Wherein, X is halogen.
7. the miscellaneous anthracene class organic compound prepared by a kind of claim 1-5 any one or claim 6 is for making
Have the application of organic electroluminescence devices.
8. application according to claim 7, which is characterized in that the organic electroluminescence device includes at least one layer of function
The miscellaneous anthracene class organic compound that layer is prepared containing claim 1-5 any one or claim 6.
9. application according to claim 7, which is characterized in that the organic electroluminescence device, including electronic barrier layer,
The electronic blocking layer material is that the miscellaneous anthracene class prepared by claim 1-5 any one or claim 6 organises
Close object.
10. application according to claim 7, which is characterized in that the organic electroluminescence device, including luminescent layer, institute
It states luminescent layer and contains the miscellaneous anthracene class organic compound prepared by claim 1-5 any one or claim 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910323721.9A CN109942578B (en) | 2019-04-22 | 2019-04-22 | Organic compounds of heteroanthracene class, preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910323721.9A CN109942578B (en) | 2019-04-22 | 2019-04-22 | Organic compounds of heteroanthracene class, preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109942578A true CN109942578A (en) | 2019-06-28 |
| CN109942578B CN109942578B (en) | 2020-10-27 |
Family
ID=67014558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910323721.9A Active CN109942578B (en) | 2019-04-22 | 2019-04-22 | Organic compounds of heteroanthracene class, preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109942578B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111170942A (en) * | 2020-01-17 | 2020-05-19 | 苏州大学 | Preparation and application of chiral (R/S) -9-methyl-2, 9-diphenyl-9, 10-dihydroacridine derivative |
| CN111763205A (en) * | 2020-01-15 | 2020-10-13 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
| CN113072554A (en) * | 2021-03-29 | 2021-07-06 | 武汉华星光电半导体显示技术有限公司 | Organic compound, manufacturing method thereof and display panel |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749050A (en) * | 2016-12-15 | 2017-05-31 | 中节能万润股份有限公司 | A kind of hot activation delayed fluorescence OLED material and its application with cyclic diketones as core |
| CN107056809A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of organic compound containing dimethylanthracene and its applied on organic electroluminescence device |
| CN107068888A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of organic electroluminescence device containing ketone and heterocyclic nitrogen compound and its application |
| CN107868048A (en) * | 2016-09-28 | 2018-04-03 | 江苏三月光电科技有限公司 | A kind of compound containing fluorenes and its application |
| WO2018152436A1 (en) * | 2017-02-17 | 2018-08-23 | University Of Research Foundation, Incorporated | Phenazine derivatives as antimicrobial agents |
| WO2018160003A1 (en) * | 2017-02-28 | 2018-09-07 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting device comprising same |
| CN109336812A (en) * | 2018-10-11 | 2019-02-15 | 吉林奥来德光电材料股份有限公司 | Organic luminescent compounds and preparation method thereof and organic electroluminescence device containing the compound |
-
2019
- 2019-04-22 CN CN201910323721.9A patent/CN109942578B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107056809A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of organic compound containing dimethylanthracene and its applied on organic electroluminescence device |
| CN107068888A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of organic electroluminescence device containing ketone and heterocyclic nitrogen compound and its application |
| CN107868048A (en) * | 2016-09-28 | 2018-04-03 | 江苏三月光电科技有限公司 | A kind of compound containing fluorenes and its application |
| CN106749050A (en) * | 2016-12-15 | 2017-05-31 | 中节能万润股份有限公司 | A kind of hot activation delayed fluorescence OLED material and its application with cyclic diketones as core |
| WO2018152436A1 (en) * | 2017-02-17 | 2018-08-23 | University Of Research Foundation, Incorporated | Phenazine derivatives as antimicrobial agents |
| WO2018160003A1 (en) * | 2017-02-28 | 2018-09-07 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting device comprising same |
| CN109336812A (en) * | 2018-10-11 | 2019-02-15 | 吉林奥来德光电材料股份有限公司 | Organic luminescent compounds and preparation method thereof and organic electroluminescence device containing the compound |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763205A (en) * | 2020-01-15 | 2020-10-13 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
| CN111170942A (en) * | 2020-01-17 | 2020-05-19 | 苏州大学 | Preparation and application of chiral (R/S) -9-methyl-2, 9-diphenyl-9, 10-dihydroacridine derivative |
| CN113072554A (en) * | 2021-03-29 | 2021-07-06 | 武汉华星光电半导体显示技术有限公司 | Organic compound, manufacturing method thereof and display panel |
| WO2022205588A1 (en) * | 2021-03-29 | 2022-10-06 | 武汉华星光电半导体显示技术有限公司 | Organic compound and manufacturing method therefor, and display panel |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109942578B (en) | 2020-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI593684B (en) | The organic electroluminescent material and organic electroluminescence device | |
| CN107021926A (en) | A kind of compound containing azepine spiro fluorene and nitrogenous hexa-member heterocycle and its application on OLED | |
| JP2016034935A (en) | Tridentate cyclometalated metal complexes with six-membered coordination rings | |
| CN107056783A (en) | A kind of compound containing azepine spiro fluorene and nitrogenous hexa-member heterocycle and its application on organic electroluminescence device | |
| CN109942578A (en) | Miscellaneous anthracene class organic compound and its preparation method and application | |
| CN109293516B (en) | Triarylamine compound and organic light-emitting device thereof | |
| CN109942637B (en) | Metal complex and organic electroluminescent device | |
| CN109928936B (en) | Organic electroluminescent compounds and use thereof | |
| CN108276336A (en) | A kind of organic photoelectric functional material and luminescent device and its preparation method and application | |
| TWI641598B (en) | Compound and organic electronic device using the same | |
| CN107602397B (en) | Compound with dibenzosuberene as core and application thereof | |
| CN106749320B (en) | A kind of benzimidazole simultaneously ketone compounds and its application in OLED device | |
| CN109574931A (en) | A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and its application on organic electroluminescence device | |
| CN111423390A (en) | Novel structural compound and application thereof | |
| CN109574930A (en) | A kind of compound of nitrogen-containing hetero heptatomic ring derivative, preparation method and applications | |
| CN109748916A (en) | It is a kind of using azepine spiro fluorene and aryl ketones as the compound of core, preparation method and its application on OLED | |
| KR20180018382A (en) | Compound and organic electronic device using the same | |
| CN112778312B (en) | Organic material containing indoloquinazolinedione heterocyclic structure and application thereof | |
| CN111675714B (en) | Organic electroluminescent compound with balanced carrier transmission performance and application thereof | |
| CN103787822B (en) | Containing anthracene compounds, its preparation method and application thereof, organic luminescent device | |
| CN110655486A (en) | Compound with dibenzosuberene as core and application thereof | |
| CN110183302B (en) | Condensed terphenyl compound and preparation method and application thereof | |
| CN111548371A (en) | 1, 8-substituted carbazole-based quadridentate ring metal palladium (II) complex phosphorescent material and application | |
| CN113735827B (en) | Compound, organic electroluminescent device and display device | |
| CN113735831B (en) | Compound, intermediate, preparation method of compound and intermediate, and organic electroluminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |