CN102443001A - Organic luminescent material 4, 6-diphenyl-1, 9-anthralin compound, synthetic method and application - Google Patents
Organic luminescent material 4, 6-diphenyl-1, 9-anthralin compound, synthetic method and application Download PDFInfo
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- CN102443001A CN102443001A CN2010105010228A CN201010501022A CN102443001A CN 102443001 A CN102443001 A CN 102443001A CN 2010105010228 A CN2010105010228 A CN 2010105010228A CN 201010501022 A CN201010501022 A CN 201010501022A CN 102443001 A CN102443001 A CN 102443001A
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- anthralin
- phenylbenzene
- methyl alcohol
- compound
- dibenzoyl
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- 229960002311 dithranol Drugs 0.000 title abstract description 66
- 239000000463 material Substances 0.000 title abstract description 14
- 238000010189 synthetic method Methods 0.000 title 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000006482 condensation reaction Methods 0.000 claims abstract description 3
- 229940100630 metacresol Drugs 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical class C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 abstract description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 abstract description 2
- IBASEVZORZFIIH-UHFFFAOYSA-N 1-(9h-fluoren-2-yl)ethanone Chemical group C1=CC=C2C3=CC=C(C(=O)C)C=C3CC2=C1 IBASEVZORZFIIH-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- CNILDPCFXDESRI-UHFFFAOYSA-N 1-(9h-carbazol-3-yl)ethanone Chemical group C1=CC=C2C3=CC(C(=O)C)=CC=C3NC2=C1 CNILDPCFXDESRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 180
- 239000000243 solution Substances 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000013019 agitation Methods 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 20
- 238000010790 dilution Methods 0.000 description 20
- 239000012895 dilution Substances 0.000 description 20
- 238000001035 drying Methods 0.000 description 20
- 238000001556 precipitation Methods 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 20
- 238000005406 washing Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 238000002189 fluorescence spectrum Methods 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- -1 Anthralin small molecules Chemical class 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 0 *c(cc(-c1ccccc1)c1c2)nc1cc1c2nc(*)cc1-c1ccccc1 Chemical compound *c(cc(-c1ccccc1)c1c2)nc1cc1c2nc(*)cc1-c1ccccc1 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- WDVHCEPEJVUJPE-UHFFFAOYSA-N 1-(9-dodecylcarbazol-3-yl)ethanone Chemical compound CC(=O)C1=CC=C2N(CCCCCCCCCCCC)C3=CC=CC=C3C2=C1 WDVHCEPEJVUJPE-UHFFFAOYSA-N 0.000 description 1
- AAMBQMDRFSEKOF-UHFFFAOYSA-N 1-(9-ethylcarbazol-3-yl)ethanone Chemical compound CC(=O)C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 AAMBQMDRFSEKOF-UHFFFAOYSA-N 0.000 description 1
- PKGYERNSXJOSJQ-UHFFFAOYSA-N 1-[4-(4-butylphenyl)phenyl]ethanone Chemical group C1=CC(CCCC)=CC=C1C1=CC=C(C(C)=O)C=C1 PKGYERNSXJOSJQ-UHFFFAOYSA-N 0.000 description 1
- UMLWXYJZDNNBTD-UHFFFAOYSA-N 2-(dimethylamino)-1-phenylethanone Chemical compound CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 1
- HRVQMQWVGKYDCF-UHFFFAOYSA-N 2-Acetyl-4-methylpyridine Chemical compound CC(=O)C1=CC(C)=CC=N1 HRVQMQWVGKYDCF-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 1
- CHAUXBYGEJXENI-UHFFFAOYSA-N C(C)C(=O)CC.C(C)C1=CC=CC=C1 Chemical compound C(C)C(=O)CC.C(C)C1=CC=CC=C1 CHAUXBYGEJXENI-UHFFFAOYSA-N 0.000 description 1
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 description 1
- QCWXDVFBZVHKLV-UHFFFAOYSA-N CC(C)(C)c1ccc(C)cc1 Chemical compound CC(C)(C)c1ccc(C)cc1 QCWXDVFBZVHKLV-UHFFFAOYSA-N 0.000 description 1
- UAAZICLDKZHVHK-UHFFFAOYSA-N CCCCCCc1ccc(-c2ccc(C)[s]2)[s]1 Chemical compound CCCCCCc1ccc(-c2ccc(C)[s]2)[s]1 UAAZICLDKZHVHK-UHFFFAOYSA-N 0.000 description 1
- BCJOBVWKIGRZCW-UHFFFAOYSA-N CCCCCCc1ccc(C)cc1 Chemical compound CCCCCCc1ccc(C)cc1 BCJOBVWKIGRZCW-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- CHLICZRVGGXEOD-UHFFFAOYSA-N Cc(cc1)ccc1OC Chemical compound Cc(cc1)ccc1OC CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a 4, 6-diphenyl-1, 9-anthralin compound luminescent material, a preparation method and application thereof. The invention takes 4, 6-dibenzoyl-1, 3-m-phenylenediamine, p-alkylacetophenone, p-acetylbiphenyl, p-acetyldiphenyl ether, 2-acetylfluorene, 3-acetylcarbazole and alkyl substituted monoacetyl compounds thereof as raw materials, uses polyphosphoric acid as a catalyst, and uses m-cresol as a solvent to carry out Friedlander condensation reaction to obtain a series of 4, 6-diphenyl-1, 9 anthralin compounds. The compound can be used as a light-emitting layer or an electron transport layer of an organic light-emitting diode.
Description
Technical field
The invention belongs to the photovaltaic material technical field.Be specifically related to a kind of 4,6-phenylbenzene-1,9-anthralin compounds, compound method and application.Said compound has luminescent properties, can be used as the luminescent layer or the electron transfer layer of Organic Light Emitting Diode.
Technical background
Organic light emitting diodde desplay device (Organic light-emitting diode; OLED), will become the strong rival of light source of new generation and flat-panel monitor because of advantages such as it have the luminosity height, driving voltage is low, power consumption is little, response speed is fast, sharpness is high, can realize panchromatic demonstration, technology is simple.In recent years, aspect of performances such as the glow color of the main ctc OLED of research in organic thin film electroluminescent field, the efficient that improves device and life-span, comprise optimised devices ME, exploitation novel material, inquire into device surface interaction mechanism etc.(Tang C W since the reported first OLED of Kodak in 1987; Vanslyke S A.Applied Physics Letters, 1987,51; 913.), the luminous organic material that research and development has fluorescent yield height, a good stability just becomes one of the focus of scientist's concern.
Luminous organic material mainly is divided into organic molecule luminescent material and high-molecular luminous material two big classes.The organic molecule luminescent material has that chemically modified property is strong, range of choice is wide, be easy to purify, high (the Ching-Hsin Chen F-I W of fluorescence quantum efficiency; Ching-Fong Shu; Et al.Spirobifluorene-based pyrazoloquinolines:efficient blue electroluminescent materials.Journal of Materials Chemistry; 2004,145.) and can produce versicolor light (Yun-Hi Kim D-C S, Sung-Han Kim such as RGB; Et al.Novel Blue Emitting Material with High Color Purity.Advanced Materials; 2001,13, characteristics 4.).But its fluorescence quantum efficiency, solvability, stability are desirable not enough; Thereby in film process, be prone to pin hole and can't realize the making of large area display spare (Liu S, Jiang P, Song G L; Et al.Synthesis and optical properties of a series of thermally stable diphenylanthrazolines.Dyes and Pigments; 2009,81,218.).For addressing the above problem, people's design, synthetic polytype small molecules and verivate thereof (like anthracene and phenyl replaces anthracene derivant ， perylene Ji the perylene analog derivative, fluorenes and verivate thereof, title complex luminous organic materials such as oxine aluminium, etc.).
In recent years, the application of anthralin compounds aspect luminous organic material obtained the concern of scientists.2003, Jenekhe research group of Washington, DC university reported 5 anthralin micromolecular compounds and at application (Tonzola C J, the Alam M M in electroluminescent field; Kaminsky W, et al.New n-type organic semiconductors:Synthesis, single crystal structures; Cyclic voltammetry, photophysics, electron transport; And electroluminescence of a series of diphenylanthrazolines.J Am Chem Soc; 2003,125:13548.), structural formula is following.2009,
Hongjun ZHU professor research group of Nanjing University of Technology has reported 9 anthralin micromolecular compounds and relevant chemical research (the Liu S of optical physics thereof as follows; Jiang P; Song G L, et al.Synthesis and optical properties of a series of thermally stable diphenylanthrazolines.Dyes and Pigments, 2009; 81,218.).
Anthralin small molecules and polymkeric substance thereof have outstanding thermostability; Satisfied the basic demand of electron device to resistance toheat; The anthralin agent structure has bigger π-electron conjugated system simultaneously; Cause the electronics in such molecular structure that delocalization largely can take place, have lower energy gap (E
g), be a kind of comparatively ideal electron transport material.These essential propertys are further design, synthetic anthralin compounds, and character and the application of studying this compounds simultaneously provide foundation.But the solvability of the anthralin micromolecular compound of above-mentioned report is not fine, has influenced their some performance tests and their further developing in the OLED field.Therefore; For the solvability that solves anthralin micromolecular compound is not good problem; It is a series of 4 that this seminar design has been synthesized, 6-phenylbenzene-1,9-anthralin compounds luminous organic material; Hope can solve the solubility problem of this compounds preferably under the prerequisite of guaranteeing fluorescence quantum efficiency that they are outstanding and thermostability.And our research proof 4; 6-phenylbenzene-1; The solvability of 9-anthralin compounds is greatly improved really, and this further develops the OLED material with good luminous performance, film forming properties and higher external quantum efficiency to us and has important significance for theories and actual guiding value.
Summary of the invention
The objective of the invention is to propose one type have good electron transport ability and luminescent properties, contain chromophore or auxochromes 4; 6-phenylbenzene-1,9-anthralin compounds, compound method, with and as the application of the luminescent layer or the electron transfer layer of Organic Light Emitting Diode.
The present invention is with 4, and 6-phenylbenzene-1,9-anthralin are that main body is carried out structural modification, obtain a series of 4,6-phenylbenzene-1,9-amidine anthralin compounds.Through introducing flexible alkyl chain, to improve its solvability; Through introducing auxochrome group or chromophoric group increase conjugate length such as aromatic group or heteroaromatic group; To increase the delocalization ability of its π system electronic cloud; Thereby the raising electron transport ability improves fluorescence quantum efficiency, changes its chemical property, solvability, luminescent properties and electronics property; Increase system stability is improved its application performance.
Among the present invention, with 4 of 1 times of amount (amount of substance is a unit, down together), 6-dibenzoyl-1; The monoacylphosphine compound of 3-mphenylenediamine and 1: 2.0 to 1: 2.4 times amount adopts polyphosphoric acid catalyzed dose, is solvent with the meta-cresol, under 100 ℃ to 170 ℃ condition, carries out the Friedlander condensation reaction 20-145 hour; Obtain a series of 4,6-phenylbenzene-1,9-anthralin compounds; Obtain comparatively satisfied yield (during top condition, yield is more than 60%) simultaneously, reaction formula is:
Wherein, R is:
Wherein, R
1Alkyl, carbonatoms 7 to 12 aromatic bases for H, carbonatoms 1 to 12.
In the above-claimed cpd structure, more typically there are following several kinds:
(1) 2,8-two (substituted-phenyl)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Alkyl, the alkoxyl group of carbonatoms 1-6, nitro, dimethylamino for carbonatoms 1-6.
(2) 2,8-two (substituted biphenyl base)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Be H.
(3) 2,8-two (substituted diphenylamine ether)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Be H.
(4) 2,8-two (replacement fluorenyl)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Alkyl substituent, normal heptane base, dodecyl for H, carbonatoms 1-6.
(5) 2,8-two (substituted carbazole base)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Alkyl substituent, normal heptane base, dodecyl for H, carbonatoms 1-6.
(6) 2,8-two (substituted pyridinyl)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Be H, methyl, ethyl, normal-butyl.
(7) 2,8-two (substituted thiophene base)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Be H, methyl, ethyl, normal-butyl.
(8) 2,8-two (replacing the triphen amido)-4,6-phenylbenzene-1,9-anthralin
R wherein
1Be H, methyl, ethyl, normal-butyl.
Wherein, typical compound 2,4,6,8-tetraphenyl-1,9-anthralin, 2; 8-two (to tert-butyl-phenyl)-4,6-phenylbenzene-1,9-anthralin, 2,8-two (p-methoxyphenyl)-4,6-phenylbenzene-1,9-anthralin, 2; 8-two (4 '-the triphen amido)-4,6-phenylbenzene-1,9-anthralin, 2,8-two (4 '-xenyl)-4,6-phenylbenzene-1,9-anthralin, 2; 8-two (4 '-the hexichol ether)-4,6-phenylbenzene-1,9-anthralin, 2,8-two (4 '-(9 " carbazyl) phenyl)-4,6-phenylbenzene-1,9-anthralin, 2; 8-two (2 '-fluorenyl)-4,6-phenylbenzene-1,9-anthralin, 2,8-two (3 '-the N-ethyl carbazole)-4,6-phenylbenzene-1, the 9-anthralin (
1a-
1h) ultraviolet maximum absorption wavelength between 397-454nm, maximum fluorescence emission spectrum is between 532-493nm, peak width at half is about 50nm (concrete spectral quality see table 1), is one type of ideal blue light organic luminescent material.
Description of drawings
Fig. 1
1a-
1hUltraviolet-visible absorption spectroscopy in the toluene solution (c=5.0 * 10
-5Mol L
-1)
Fig. 2
1a-
1hFluorescence emission spectrum in the toluene solution (c=5.0 * 10
-8Mol L
-1)
Embodiment
Embodiment 1:2,4,6,8-tetraphenyl-1, the 9-anthralin (
1a) synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), methyl phenyl ketone 0.5046g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange-yellow chip solid 2,4,6; 8-tetraphenyl-1,9-anthralin (1a) 0.78g, yield 80.5%; 265.4 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 2:2,8-two (to tert-butyl-phenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1b) synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), p-tert.-butyl acetophenone 0.7402g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow chip solid 2,8-two (to tert-butyl-phenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1b) 0.72g, yield 60.4%, 280.9 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 3:2,8-two (p-methoxyphenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1c) synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), p-methoxy-acetophenone 0.6303g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain glassy yellow needle-like solid 2,8-two (p-methoxyphenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1c) 0.70g, yield 64.3%, 266.5 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 4:2,8-two (4 '-the triphen amido)-4,6-phenylbenzene-1, the 9-anthralin (
1d) synthetic
4,6-dibenzoyl-1, the 3-mphenylenediamine (0.6328g, 2.0mmol), 4 '-ethanoyl triphenylamine 1.2059g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange/yellow solid powder 2,8-two (4 '-the triphen amido)-4,6-phenylbenzene-1, the 9-anthralin (
1d) 1.33g, yield 81.2%, 294.1 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 5:2,8-two (4 '-biphenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1e) synthetic
4,6-dibenzoyl-1, the 3-mphenylenediamine (0.6328g, 2.0mmol), 4 '-acetyl biphenyl 0.8240g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow chip solid 2,8-two (4 '-biphenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1e) 1.21g, yield 94.9%, 267.2 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 6:2,8-two (4 '-the hexichol ether)-4,6-phenylbenzene-1, the 9-anthralin (
1f) synthetic
4,6-dibenzoyl-1, the 3-mphenylenediamine (0.6328g, 2.0mmol), 4 '-ethanoyl phenyl ether 0.8907g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain glassy yellow needle-like solid 2,8-two (4 '-the hexichol ether)-4,6-phenylbenzene-1, the 9-anthralin (
1f) 1.01g, yield 75.6%, 215.1 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 7:2,8-two (4 '-(9 " carbazyl) phenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1g) synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), 4-(9 '-carbazyl) methyl phenyl ketone 1.1975g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow solid powder 2,8-two (4 '-(9 " carbazyl) phenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1g) 1.05g, yield 64.5%, 225.8 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 8:2,8-two (2 '-fluorenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1h) synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), 2-ethanoyl fluorenes 0.8740g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow solid powder 2,8-two (2 '-fluorenyl)-4,6-phenylbenzene-1, the 9-anthralin (
1h) 0.81g, yield 61.4%, 307.6 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 9:2,8-two (3 '-N-ethyl carbazole base)-4,6-phenylbenzene-1, the 9-anthralin (
1i) synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), 3-ethanoyl-N-ethyl carbazole 0.9959g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow chip solid 2,8-two (3 '-N-ethyl carbazole base)-4,6-phenylbenzene-1, the 9-anthralin (
1i) 1.01g, yield 70.3%, 322.8 ℃ of fusing points, uv absorption spectrum is seen accompanying drawing 1, fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 10:2,8-two (p-methylphenyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), p-methyl aceto phenone 0.5636g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange-yellow chip solid 2,8-two (p-methylphenyl)-4,6-phenylbenzene-1,9-anthralin 0.73g, yield 71.6%.
Embodiment 11:2,8-two (to ethylphenyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g 2.0mmol), is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions ethylbenzene ethyl ketone 0.6224g (4.2mmol) the 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange-yellow chip solid 2,8-two (to ethylphenyl)-4,6-phenylbenzene-1,9-anthralin 0.83g, yield 76.6%.
Embodiment 12:2,8-two (4 '-N, the N-dimethylamino phenyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), to N, N-dimethylamino methyl phenyl ketone 0.6855g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange red particulate solid 2,8-two (4 '-N, the N-dimethylamino phenyl)-4,6-phenylbenzene-1,9-anthralin 0.78g, yield 68.3%.
Embodiment 13:2,8-two (2 '-pyridyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), 2-acetylpyridine 0.5088g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow chip solid 2,8-two (2 '-pyridyl)-4,6-phenylbenzene-1,9-anthralin 0.58g, yield 59.7%.
Embodiment 14:2,8-two (2 '-thienyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), 2-acetyl thiophene 0.5300g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow solid powder 2,8-two (2 '-thienyl)-4,6-phenylbenzene-1,9-anthralin 0.67g, yield 67.4%.
Embodiment 15:2,8-two (9 ', 9 '-two normal heptane base fluorenyls)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1,3-mphenylenediamine (0.6328g; 2.0mmol), 9,9-two normal heptanes base-2-acetyl thiophene 1.6990g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions; Magnetic agitation, temperature control 130-140 ℃, reaction 116h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange/yellow solid powder 2,8-two (9 ', 9 '-two normal heptane base fluorenyls)-4,6-phenylbenzene-1,9-anthralin 1.31g, yield 62.2%.
Embodiment 16:2,8-two (4 '-normal-butyl xenyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1,3-mphenylenediamine (0.6328g; 2.0mmol), 4-normal-butyl-4 '-acetyl biphenyl 1.0600g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions magnetic agitation; Temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow solid powder 2,8-two (4 '-the normal-butyl xenyl)-4,6-phenylbenzene-1,9-anthralin 1.03g, yield 68.8%.
Embodiment 17:2,8-two (4 '-picolyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), 4-methyl-2-acetylpyridine 0.5677g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow chip solid 2,8-two (4 '-picolyl)-4,6-phenylbenzene-1,9-anthralin 0.59g, yield 57.3%.
Embodiment 18:2,8-two (4 '-methyldiphenyl ether)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, the 3-mphenylenediamine (0.6328g, 2.0mmol), 4-methyl-4 '-acetyl phenyl ether 0.9503g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow needle-like solid 2,8-two (4 '-the methyldiphenyl ether)-4,6-phenylbenzene-1,9-anthralin 0.66g, yield 47.3%.
Embodiment 19:2,8-two (3 '-N-dodecyl carbazyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1,3-mphenylenediamine (0.6328g; 2.0mmol), N-dodecyl-3-acetyl carbazole 1.5860g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions, magnetic agitation; Temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow chip solid 2,8-two (3 '-N-dodecyl carbazyl)-4,6-phenylbenzene-1,9-anthralin 1.11g, yield 52.9%.
Embodiment 20:2,8-two (p-nitrophenyl)-4,6-phenylbenzene-1,9-anthralin synthetic
4,6-dibenzoyl-1, (0.6328g, 2.0mmol), p-nitroacetophenone 0.6814g (4.2mmol) is added in polyphosphoric acid (4.2g) and meta-cresol (10ml) mixing solutions 3-mphenylenediamine, magnetic agitation, temperature control 130-140 ℃, reaction 50h.Be cooled to 80 ℃ then,, pour 1molL into methyl alcohol (50ml) dilution
-1The KOH aqueous solution (500ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 500ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain orange pressed powder 2,8-two (p-nitrophenyl)-4,6-phenylbenzene-1,9-anthralin 0.62g, yield 54.2%.
Table 1.
1a-
1iThe spectral quality tabulation
Table?1.Spectra?properties?of?
1a-
1i
Though the present invention has been detailed, yet it is not to be used to limit the present invention with preferred embodiment.Any those skilled in the art under the situation that does not break away from the spirit and scope of the present invention, should make various modifications and change.Therefore protection scope of the present invention should be regarded as appended claims institute restricted portion.
Claims (6)
1. one kind 4,6-phenylbenzene-1,9-anthralin compounds is characterized in that general structure I is following:
Wherein, R is:
Wherein, R
1Alkyl, carbonatoms 6 to 12 aromatic bases for H, carbonatoms 1 to 12.
One kind as claimed in claim 14,6-phenylbenzene-1, the compound method of 9-anthralin compounds; It is characterized in that: with 4 of 1 times of amount (amount of substance is a unit, down together), 6-dibenzoyl-1; 3-mphenylenediamine and monoacylphosphine compound polyphosphoric acid catalyzed dose with the meta-cresol mixing solutions in, under 100 ℃ to 170 ℃ condition, carry out the Friedlander condensation reaction, obtain a series of 4; 6-phenylbenzene-1,9-anthralin compounds.
3. a compound method as claimed in claim 2 is characterized in that 4,6-dibenzoyl-1, and the 3-mphenylenediamine is 1: 2.0 to 1: 2.4 with the amount ratio of monoacylphosphine compound RM, optimum proportion is 1: 2.1.
4. a compound method as claimed in claim 2 is characterized in that the polyphosphoric acid catalyzed dose of mass ratio with meta-cresol is 1: 1 to 1: 5, and optimum proportion is 1: 2.4.
5. a compound method as claimed in claim 3 is characterized in that the reaction times is 20 to 145 hours, and optimum reacting time is 40-60 hour.
One kind as claimed in claim 14,6-phenylbenzene-1, the application of 9-anthralin compounds can be used for the luminescent layer or the electron transfer layer of Organic Light Emitting Diode.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105669670A (en) * | 2016-03-04 | 2016-06-15 | 吉林奥来德光电材料股份有限公司 | Heterocyclic compound and preparation method thereof as well as organic electroluminescent device |
| CN107867748A (en) * | 2016-09-28 | 2018-04-03 | 南京工业大学 | Method for treating methylene blue wastewater by photocatalytic oxidation of organic semiconductor diphenyl anthraoxazoline compound |
| CN107936014A (en) * | 2017-12-17 | 2018-04-20 | 南京科技职业学院 | The synthetic method of the double indeno anthracene oxazolines of 4,6 diphenyl of luminous organic material and application |
| CN110437627A (en) * | 2018-05-04 | 2019-11-12 | 中国石油化工股份有限公司 | A kind of modifying agent mother liquor and road asphalt and preparation method thereof |
| CN110665544A (en) * | 2019-10-25 | 2020-01-10 | 广州市骏辉环保科技有限公司 | Preparation method and application of organic semiconductor photocatalyst |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669670A (en) * | 2016-03-04 | 2016-06-15 | 吉林奥来德光电材料股份有限公司 | Heterocyclic compound and preparation method thereof as well as organic electroluminescent device |
| CN107867748A (en) * | 2016-09-28 | 2018-04-03 | 南京工业大学 | Method for treating methylene blue wastewater by photocatalytic oxidation of organic semiconductor diphenyl anthraoxazoline compound |
| CN107867748B (en) * | 2016-09-28 | 2020-11-17 | 南京工业大学 | Method for treating methylene blue wastewater by photocatalytic oxidation of organic semiconductor diphenyl anthraoxazoline compound |
| CN107936014A (en) * | 2017-12-17 | 2018-04-20 | 南京科技职业学院 | The synthetic method of the double indeno anthracene oxazolines of 4,6 diphenyl of luminous organic material and application |
| CN110437627A (en) * | 2018-05-04 | 2019-11-12 | 中国石油化工股份有限公司 | A kind of modifying agent mother liquor and road asphalt and preparation method thereof |
| CN110437627B (en) * | 2018-05-04 | 2021-05-04 | 中国石油化工股份有限公司 | Modifier mother liquor, road asphalt and preparation method thereof |
| CN110665544A (en) * | 2019-10-25 | 2020-01-10 | 广州市骏辉环保科技有限公司 | Preparation method and application of organic semiconductor photocatalyst |
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