CN102443004A - Organic luminescent material 6,7,14,15-tetrahydro-5,13-disubstituted benzene [1,2-c:4,5-c']bis-acridine compound, its synthesis method and its application - Google Patents
Organic luminescent material 6,7,14,15-tetrahydro-5,13-disubstituted benzene [1,2-c:4,5-c']bis-acridine compound, its synthesis method and its application Download PDFInfo
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- CN102443004A CN102443004A CN2011103376997A CN201110337699A CN102443004A CN 102443004 A CN102443004 A CN 102443004A CN 2011103376997 A CN2011103376997 A CN 2011103376997A CN 201110337699 A CN201110337699 A CN 201110337699A CN 102443004 A CN102443004 A CN 102443004A
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- tetrahydrochysene
- amerantrone
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- benzo
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- 239000000463 material Substances 0.000 title abstract description 11
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 8
- 238000001308 synthesis 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 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 20
- -1 o-aminophenyl ketone compound Chemical class 0.000 claims abstract description 17
- 150000001555 benzenes Chemical class 0.000 claims abstract description 12
- 238000006482 condensation reaction Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract 2
- 150000001251 acridines Chemical class 0.000 claims description 42
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 21
- 229940100630 metacresol Drugs 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 abstract 1
- 239000003054 catalyst Substances 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 90
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 238000013019 agitation Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- 238000001556 precipitation Methods 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000002189 fluorescence spectrum Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical class C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FLORUWDSYNSEAH-UHFFFAOYSA-N (2-aminophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1N FLORUWDSYNSEAH-UHFFFAOYSA-N 0.000 description 1
- RMMJUQSANCPTMV-UHFFFAOYSA-N (2-aminophenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1N RMMJUQSANCPTMV-UHFFFAOYSA-N 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 0 Cc1ccc(*2c(cccc3)c3-c3c2cccc3)cc1 Chemical compound Cc1ccc(*2c(cccc3)c3-c3c2cccc3)cc1 0.000 description 1
- ULESYUQFBINNPY-UHFFFAOYSA-N [2-(2-aminophenyl)phenyl]-phenylmethanone Chemical compound NC1=C(C=CC=C1)C1=C(C(=O)C2=CC=CC=C2)C=CC=C1 ULESYUQFBINNPY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- DEPZYPUUODYSIZ-UHFFFAOYSA-N aniline;butan-2-one Chemical group CCC(C)=O.NC1=CC=CC=C1 DEPZYPUUODYSIZ-UHFFFAOYSA-N 0.000 description 1
- QPOWUYJWCJRLEE-UHFFFAOYSA-N dipyridin-2-ylmethanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=N1 QPOWUYJWCJRLEE-UHFFFAOYSA-N 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
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Abstract
The invention provides a 6,7,14,15-tetrahydro-5,13-disubstituted benzene [1,2-c:4,5-c']bis-acridine compound luminescent material, its preparation method and its application. According to the invention, a 1,2,3,4,5,6,7,8-tetrahydro-1,5-anthracenedione and o-aminophenyl ketone compound is taken as a raw material, polyphosphoric acid is taken as a catalyst, m-cresol is taken as a solvent for Friedlander condensation reaction to obtain a series of the 6,7,14,15-tetrahydro-5,13-disubstituted benzene [1,2-c:4,5-c']bis-acridine compound. The compound can be taken as a luminescent layer or an electronic transmission 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 ofly 6,7,14,15-tetrahydrochysene-5,13-disubstituted benzenes be [1,2-c:4,5-c '] two acridine compounds, compound method and application also.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) because of it has advantages such as luminosity height, driving voltage is low, volume is little, response speed is fast, resolving power is high, plate thickness is thin, become the strongest rival of flat panel display device of future generation.(Tang C W since the reported first OLED of Kodak in 1987; Vanslyke S A.Applied Physics Letters, 1987,51; 913.), the research and development of luminous organic material with fluorescent yield height, good stability is just become scientist's research focus.
Luminous organic material mainly is divided into two big types of organic molecule luminescent material, high-molecular luminous materials.Wherein,, make nitrogenous compound that electronic mobility preferably arranged because nitrogen-atoms has a pair of lone-pair electron, and in luminous organic material by extensive studies.
Nitrogenous compound is one type of important luminescent material; Already by the deep research of people, and the synthetic luminous organic material preferably that obtains, like the aromatic amine compounds BFA-1T of people such as calendar year 2001 Kenji Okumoto report; Be one and have good thermal stability blue light material (Kenji Okumoto; Takahiro Ohara, Tesuya Noda, Yasuhiko Shirota.A thermally stable greenish blue organic electroluminescent device using a novel emitting amorphous molecular material.Synthetic Metals.2001; 121,1655).
Contain the azepine polycyclic compound and receive extensive attention in recent years as a kind of luminous organic material; For example people such as Tonzola reported four kinds of oligomeric quinoline (Christopher J.Tonzola, Abhishek P.Kulkarni, Angela P.Gifford that its structural formula is following in 2007; Werner Kaminsky; And Samson A.Jenekhe:Blue-light-emitting oligoquinolines:synthesis, properties, and high-efficiency blue-light-emitting diodes.Adv.Funct.Mater.2007; 17; 863), this compounds heat stable property good (Tg >=133 ℃), fluorescence quantum efficiency high (0.73-0.94), and also fluorescence emission spectrum be a blueness.
Anthralin class azapolycyclic compound has also received people's attention in recent years.This seminar had reported 9 anthralin micromolecular compounds and relevant optical physics chemical property (Liu S thereof as follows in 2009; Jiang P, Song G L, et al.Synthesis and optical properties of a series of thermally stable diphenylanthrazolines.Dyes and Pigments; 2009; 81,218.), this compounds has outstanding thermostability; Having satisfied the basic demand of electron device to resistance toheat, is one type of blue light material with potential application.
The acridine azapolycyclic compound also is one type of important luminous organic material.People such as Fadhel in 2009 have studied a series of luminescent materials (EP2312663A1) of relevant acridine compound of following structure.
Wherein: R
1-4Independently be H, halogen, CN, replacement or unsubstituted C
1-C
20Alkyl or heteroatoms substituted alkyl, C
6-C
20Aryl or C
5-C
20Fragrant heterocycle, C
1-C
20Alkoxyl group or C
6-C
20Aryloxy; X is substituted or unsubstituted C6-C20 aryl or C
5-C
20Fragrant heterocycle.
2010, people such as the Zhang Guanghui of Nanjing Normal University reported dihydrobenzo acridine complex of iridium (DMBA) as follows
2Ir (acac) and relative photo physicochemical property (Guanghui Zhang a; Ho-Hsiu Chou; Et al.Highly efficient organic light-emitting diodes (OLEDs) based on an iridium complex with rigid cyclometalated ligand.Organic Electronics, 2010,11; 632.), this compound has higher fluorescence quantum efficiency.
This seminar condenses two acridines and a benzene together, through introducing flexible alkyl chain, to improve its solvability; Increase conjugate length through introducing auxochrome group such as aromatic group or heteroaromatic group or chromophoric group, increasing the delocalization ability of its π system electronic cloud, thereby improve electron transport ability; Improve fluorescence quantum efficiency, change its chemical property, solvability, luminescent properties and electronics property, increase system stability; Improve its application performance, design has synthesized a series of 6,7; 14,15-tetrahydrochysene-5,13-disubstituted benzenes also [1; 2-c:4,5-c '] two acridine compounds, in the hope of further improving its optical physics performance; Discover that it has organic photoelectric performance preferably, the electroluminescent organic material that further exploitation is had excellent in performance 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 6; 7; 14,15-tetrahydrochysene-5,13-disubstituted benzenes also [1; 2-c:4,5-c '] two acridine 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 6,7,14, and 15-tetrahydrochysene-benzo [1,2-c:4,5-c '] two acridines are that main body is carried out structural modification, through introducing flexible alkyl chain, to improve its solvability; Increase conjugate length through introducing auxochrome group such as aromatic group or heteroaromatic group or chromophoric group, increasing the delocalization ability of its π system electronic cloud, thereby improve electron transport ability, improve fluorescence quantum efficiency; Change its chemical property, solvability, luminescent properties and electronics property, increase system stability is improved its application performance, and design is synthetic to obtain a series of 6; 7,14,15-tetrahydrochysene-5; The 13-disubstituted benzenes is [1,2-c:4,5-c '] two acridine compounds also.
Wherein, R is :-R
1,
R
1Alkyl for H, carbonatoms 1 to 12.
Among the present invention, a certain amount of polyphosphoric acid catalyzed following 1,2,3,4; 5,6,7,8-tetrahydrochysene-1,5-amerantrone and anthranoyl base class compound carry out Friedlander condensation reaction certain hour under certain temperature of reaction in meta-cresol; Obtain a series of 6,7,14,15-tetrahydrochysene-5,13-disubstituted benzenes also [1; 2-c:4,5-c '] two acridine compounds, during top condition, yield is more than 50%.Reaction formula is:
Wherein, R is :-R
1,
R
1Alkyl for H, carbonatoms 1 to 12.
1,2,3,4,5,6,7,8-tetrahydrochysene-1, the amount ratio of 5-amerantrone and anthranoyl base class compound RM is 1: 2.0 to 1: 2.4, optimum proportion is 1: 2.1.
1,2,3,4,5,6,7,8-tetrahydrochysene-1,5-amerantrone amount of substance (mmol) and polyphosphoric acid volume (mL) are than being 1: 1.5 to 1: 2.5, optimum proportion is 1: 2; 1,2,3,4,5,6,7,8-tetrahydrochysene-1,5-amerantrone amount of substance (mmol) with meta-cresol volume (mL) than being 1: 10 to 1: 20, optimum proportion is 1: 15.
Condensation reaction time is 40 to 80 hours, and optimum reacting time is 40-60 hour.
Wherein, typical compound 6,7,14,15-tetrahydrochysene-5,13-dimethylbiphenyl [1,2-c:4,5-c '] two acridines (
1a), 6,7,14,15-tetrahydrochysene-5,13-phenylbenzene benzo [1,2-c:4,5-c '] two acridines (
1b), 6,7,14,15-tetrahydrochysene-5,13-two (4 '-pyridyl) benzo [1,2-c:4,5-c '] two acridines (
1c), 6,7,14,15-tetrahydrochysene-5,13-two (4-methoxyl group) xenyl benzo [1,2-c:4,5-c '] two acridines (
1d), 6,7,14,15-tetrahydrochysene-5,13-two (the 4-tertiary butyl) xenyl benzo [1,2-c:4,5-c '] two acridines (
1e), 6,7,14,15-tetrahydrochysene-5,13-two (4-(9-carbazyl) phenyl) benzo [1,2-c:4,5-c '] two acridines (
1f), 6,7,14,15-tetrahydrochysene-5,13-dibutyl benzo [1,2-c:4,5-c '] two acridines (
1g), 6,7,14,15-tetrahydrochysene-5,13-two (2-(9,9 '-dibutyl) fluorenyl) benzo [1,2-c:4,5-c '] two acridines (
1h) ultraviolet maximum absorption wavelength between 373-377nm, maximum fluorescence emission spectrum is between 381-389nm, peak width at half is about 50nm (concrete spectral quality see table 1), is one type of potential blue light organic luminescent material.
Description of drawings
Ultraviolet-visible absorption spectroscopy (c=5.0 * 10 in Fig. 1 .1a-1h chloroform soln
-5MolL
-1)
Fluorescence emission spectrum (c=2.5 * 10 in Fig. 2 .1a-1h chloroform soln
-6MolL
-1)
Embodiment
Embodiment 1:6,7,14,15-tetrahydrochysene-5,13-dimethylbiphenyl [1,2-c:4,5-c '] two acridines (
1a) synthetic
1,2,3,4,5,6,7,8-tetrahydrochysene-1, (0.2140g, 1.0mmol), (0.2835g 2.1mmol) is added in polyphosphoric acid (2mL) and meta-cresol (15ml) mixing solutions o-aminoacetophenone 5-amerantrone, magnetic agitation, temperature control 110-120 ℃, reaction 40h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain pale brown toner shape solid 6,7,14,15-tetrahydrochysene-9,18-dimethylbiphenyl [1,2-c:4,5-c '] two acridines (
1a) 0.2888g, yield 70.1%, fusing point be greater than 300 ℃,
1H-NMR (500MHz, CDCl
3+ THF): δ ppm8.43 (s, 4H), 8.33 (d, 2H), 8.08 (s, 2H), 7.93 (t, 2H), 3.34 (s, 4H), 3.22 (s, 4H), 3.02 (s, 6H).Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 2:6,7,14,15-tetrahydrochysene-5,13-phenylbenzene benzo [1,2-c:4,5-c '] two acridines (
1b) synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); (0.4137g 2.2mmol) is added in polyphosphoric acid (2.2mL) and meta-cresol (18ml) mixing solutions 2-aminophenyl benzophenone, magnetic agitation, temperature control 130-140 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain white powdery solid 6,7,14,15-tetrahydrochysene-5,13-phenylbenzene benzo [1,2-c:4,5-c '] two acridines (
1b) 0.3501g, yield 65.3%, fusing point be greater than 300 ℃,
1H-NMR (500MHz, CDCl
3+ THF): δ ppm8.40 (s, 2H), 8.38 (s, 2H), 8.07 (t, 2H), 7.77-7.82 (m, 4H), 7.69-7.71 (m, 6H), 7.36-7.38 (m, 4H), 3.11 (t, 4H), 3.06 (q, 4H).Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 3:6,7,14,15-tetrahydrochysene-5,13-two (4-pyridyl) benzo [1,2-c:4,5-c '] two acridines (
1c) synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); 2-aminophenyl-4 '-(0.4158g 2.2mmol) is added in polyphosphoric acid (2.2mL) and meta-cresol (18ml) mixing solutions pyridyl ketone, magnetic agitation, temperature control 110-120 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain brown powdery solid 6,7,14,15-tetrahydrochysene-5,13-two (4 '-pyridyl) benzo [1,2-c:4,5-c '] two acridines (
1c) 0.3710g, yield 68.7%, fusing point be greater than 300 ℃,
1H-NMR (500MHz, CDCl
3+ THF): δ ppm 9.15 (bs, 4H), 8.45 (bs, 4H), 8.19 (bs, 6H), 7.86 (bs, 6H), 7.86 (bs, 2H), 7.46 (bs, 2H), 3.17 (bs, 4H), 2.98 (bs, 4H).Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 4:6,7,14,15-tetrahydrochysene-5,13-two (4-methoxyl group) xenyl benzo [1,2-c:4,5-c '] two acridines (
1d) synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); (0.6363g 2.4mmol) is added in polyphosphoric acid (1.5mL) and meta-cresol (15ml) mixing solutions 2-aminophenyl-(4-methoxyl group) xenyl ketone, magnetic agitation, temperature control 140-150 ℃, reaction 50h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain faint yellow solid powder 6,7,14,15-tetrahydrochysene-5,13-two (4-methoxyl group) xenyl benzo [1,2-c:4,5-c '] two acridines (
1d) 0.4594g, yield 61.4%, fusing point be greater than 300 ℃,
1H-NMR (500MHz, CDCl
3+ THF): δ ppm 8.52 (bs, 4H), 8.06 (bs, 2H), 7.87 (d, 6H), 7.80 (t, 2H), 7.69 (d, 4H), 7.43 (d, 4H), 7.10 (d, 4H), 3.94 (s, 6H), 3.14 (s, 8H).Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 5:6,7,14,15-tetrahydrochysene-5,13-two (the 4-tertiary butyl) xenyl benzo [1,2-c:4,5-c '] two acridines (
1e) synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); (0.6909g 2.0mmol) is added in polyphosphoric acid (2.4mL) and meta-cresol (20ml) mixing solutions 2-aminophenyl-(the 4-tertiary butyl) xenyl ketone, magnetic agitation, temperature control 150-160 ℃, reaction 70h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain pale yellow colored solid powdery solid 6,7,14,15-tetrahydrochysene-5,13-two (the 4-tertiary butyl) xenyl benzo [1,2-c:4,5-c '] two acridines (
1e) 0.4976g, yield 62.2%, fusing point be greater than 300 ℃,
1H-NMR (500MHz, CDCl
3+ THF): δ ppm 8.44 (d, 4H), 8.08 (t, 2H), 7.93 (d, 4H), 7.90 (s, 2H), 7.83 (t, 2H), 7.69 (d, 4H), 7.59 (d, 4H), 7.45 (d, 4H), 3.16 (s, 8H), 1.42 (s, 18H).Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 6:6,7,14,15-tetrahydrochysene-5,13-two (4-(9-carbazyl) phenyl) benzo [1,2-c:4,5-c '] two acridines (
1f) synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); 2-aminophenyl-4 '-(0.7602g 2.0mmol) is added in polyphosphoric acid (2.5mL) and meta-cresol (20ml) mixing solutions (9-carbazyl) phenyl ketone, magnetic agitation, temperature control 160-170 ℃, reaction 80h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain faint yellow yellow powdery solid 6,7,14,15-tetrahydrochysene-5,13-two (4-(9-carbazyl) phenyl) benzo [1,2-c:4,5-c '] two acridines (
1f) 0.4512g, yield 52.1%, fusing point is greater than 300 ℃.
1H-NMR(500MHz，CDCl
3+THF)：δppm?8.48(s，2H)，8.45(d，2H)，8.23(d，3H)，8.15(t，4H)，8.01(t，4H)，7.98(s，2H)，7.94(t，2H)，7.68(d，4H)，7.65(d，4H)，7.53(q，4H)，7.39(t，2H)，3.26(s，8H)。Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 7:6,7,14,15-tetrahydrochysene-5,13-dibutyl benzo [1,2-c:4,5-c '] two acridines (
1g) synthetic
1,2,3,4,5,6,7,8-tetrahydrochysene-1, (0.2140g, 1.0mmol), (0.3717g 2.1mmol) is added in polyphosphoric acid (1.5mL) and meta-cresol (10ml) mixing solutions adjacent amino-benzene butanone the 5-amerantrone, magnetic agitation, temperature control 100-110 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain pale brown toner shape solid 6,7,14,15-tetrahydrochysene-5,13-dibutyl benzo [1,2-c:4,5-c '] two acridines (
1g) 0.3888g, yield 70.1%.Fusing point is 230-231 ℃.
1H-NMR(500MHz，CDCl
3+THF)：δppm8.33(q，6H)，8.08(t，4H)，7.96(t，2H)，3.42(t，4H)，3.34(t，4H)，3.22(t，4H)，1.75-1.81(m，4H)，1.63-1.70(m，4H)，1.08(t，6H)。Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 8:6,7,14,15-tetrahydrochysene-5,13-two (2-(9,9 '-dibutyl) fluorenyl) benzo [1,2-c:4,5-c '] two acridines (
1h) synthetic
1,2,3,4,5,6; 7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol), 2-aminophenyl-2 '-(9; 9 '-dibutyl) (0.8337g 2.1mmol) is added in polyphosphoric acid (2mL) and meta-cresol (14ml) mixing solutions fluorenyl ketone, magnetic agitation, temperature control 130-140 ℃, reaction 75h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain faint yellow solid powder 6,7,14,15-tetrahydrochysene-5,13-two (2-(9,9 '-dibutyl) fluorenyl) benzo [1,2-c:4,5-c '] two acridines (
1h) 0.5371g, yield 61.4%, fusing point is greater than 300 ℃.
1H-NMR(500MHz，CDCl
3+THF)：δppm?8.39(d，4H)，8.08(t，2H)，8.03(t，4H)，7.85-7-90(m，4H)，7.80(t，2H)，7.37(q，4H)，3.13-3.27(m，8H)，2.00-2.13(m，8H)，1.07-1.20(m，8H)，0.69-0.82(m，8H)。Uv absorption spectrum is seen accompanying drawing 1, and fluorescence emission spectrum is seen accompanying drawing 2.
Embodiment 9:6,7,14,15-tetrahydrochysene-5,13-dibiphenylyl benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); 2-aminophenyl-4 '-(0.7161g 2.2mmol) is added in polyphosphoric acid (1.8mL) and meta-cresol (15ml) mixing solutions xenyl ketone, magnetic agitation, temperature control 150-160 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain yellow powdery solid 6,7,14,15-tetrahydrochysene-5,13-dibiphenylyl benzo [1,2-c:4,5-c '] two acridine 0.4556g, yield 55.3%.
Embodiment 10:6,7,14,15-tetrahydrochysene-5,13-two (triphen amido) benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); (0.7644g 2.3mmol) is added in polyphosphoric acid (2.4mL) and meta-cresol (19ml) mixing solutions 2-aminophenyl-triphen amido ketone, magnetic agitation, temperature control 160-170 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), 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 6,7,14,15-tetrahydrochysene-5,13-two (triphen amido) benzo [1,2-c:4,5-c '] two acridine 0.4985g, yield 57.3%.
Embodiment 11:6,7,14,15-tetrahydrochysene-5,13-two (2-fluorenyl) benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); 2-aminophenyl-2 '-(0.5985g 2.1mmol) is added in polyphosphoric acid (2.4mL) and meta-cresol (19ml) mixing solutions fluorenyl ketone, magnetic agitation, temperature control 150-160 ℃, reaction 70h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain faint yellow solid powder 6,7,14,15-tetrahydrochysene-5,13-two (2-fluorenyl) benzo [1,2-c:4,5-c '] two acridine 0.4371g, yield 61.4%.
Embodiment 12:6,7,14,15-tetrahydrochysene-5,13-two (p-methylphenyl) benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); (0.4725g 2.2mmol) is added in polyphosphoric acid (2mL) and meta-cresol (15ml) mixing solutions 2-aminophenyl p-methylphenyl ketone, magnetic agitation, temperature control 100-110 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), 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 powdery solid 6,7,14,15-tetrahydrochysene-5,13-two (p-methylphenyl) benzo [1,2-c:4,5-c '] two acridine 0.3739g, yield 66.3%.
Embodiment 13:6,7,14,15-tetrahydrochysene-5,13-two (to methoxyl group) phenyl benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4,5; 6,7,8-tetrahydrochysene-1, the 5-amerantrone (0.2140g, 1.0mmol); (0.4767g 2.1mmol) is added in polyphosphoric acid (2mL) and meta-cresol (15ml) mixing solutions 2-aminophenyl p-methoxyphenyl ketone, magnetic agitation, temperature control 130-140 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), 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 powdery solid 6,7,14,15-tetrahydrochysene-5,13-two (to methoxyl group) phenyl benzo [1,2-c:4,5-c '] two acridine 0.3639g, yield 64.3%.
Embodiment 14:6,7,14,15-tetrahydrochysene-5,13-two (4-(3,6-dimethoxy-9-carbazyl) phenyl) benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4; 5,6,7,8-tetrahydrochysene-1; The 5-amerantrone (0.2140g, 1.0mmol), 2-aminophenyl-4 '-(3,6-dimethoxy-9-carbazyl) phenyl ketone (0.8862g; 2.0mmol) be added in polyphosphoric acid (2.4mL) and meta-cresol (19ml) mixing solutions magnetic agitation, temperature control 130-140 ℃, reaction 70h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain faint yellow yellow powdery solid 6,7,14; 15-tetrahydrochysene-5,13-two (4-(3,6-dimethoxy-9-carbazyl) phenyl) benzo [1; 2-c:4,5-c '] two acridine 0.4512g, yield 50.1%.
Embodiment 15:6,7,14,15-tetrahydrochysene-5,13-two (4-(3,6-di-t-butyl-9-carbazyl) phenyl) benzo [1,2-c:4,5-c '] two acridines synthetic
1,2,3,4; 5,6,7,8-tetrahydrochysene-1; The 5-amerantrone (0.2140g, 1.0mmol), 2-aminophenyl-4 '-(3,6-di-t-butyl-9-carbazyl) phenyl ketone (0.8862g; 2.3mmol) be added in polyphosphoric acid (2mL) and meta-cresol (15ml) mixing solutions magnetic agitation, temperature control 140-150 ℃, reaction 60h.Be cooled to 80 ℃ then, pour 2molL into
-1The KOH aqueous solution (300ml) in, filter collecting precipitation, reusable heat water washing 3 times (each 200ml), drying.Use methyl alcohol/THF solution (methyl alcohol/THF volume ratio is 30-60%) to carry out recrystallization 2 times at last, obtain faint yellow yellow powdery solid 6,7,14; 15-tetrahydrochysene-5,13-two (4-(3,6-di-t-butyl-9-carbazyl) phenyl) benzo [1; 2-c:4,5-c '] two acridine 0.5112g, yield 55.1%.
Table 1.
1a-
1hThe spectral quality tabulation
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 6,7,14,15-tetrahydrochysene-5,13-disubstituted benzenes be [1,2-c:4,5-c '] two acridine compounds also, it is characterized in that general structure is following:
Wherein, R is :-R
1,
R
1Be H, the alkyl of carbonatoms 1 to 12.
One kind as claimed in claim 16,7,14,15-tetrahydrochysene-5,13-disubstituted benzenes be [1,2-c:4,5-c '] two acridine application of compound also, can be used for the luminescent layer or the electron transfer layer of Organic Light Emitting Diode.
One kind as claimed in claim 16,7,14,15-tetrahydrochysene-5,13-disubstituted benzenes also [1; 2-c:4,5-c '] compound method of two acridine compounds, it is characterized in that 1,2,3; 4,5,6,7,8-tetrahydrochysene-1; 5-amerantrone and o-amino benzoyl ketone compounds are that solvent at 100 ℃ to 170 ℃ the Friedlander condensation reaction takes place polyphosphoric acid catalyzed following with the meta-cresol, obtain 6,7,14 behind the certain hour; 15-tetrahydrochysene-5,13-disubstituted benzenes be [1,2-c:4,5-c '] two acridine compounds also.
4. a compound method as claimed in claim 3 is characterized in that 1,2,3,4,5,6,7,8-tetrahydrochysene-1, and the amount ratio of 5-amerantrone and anthranoyl base class compound RM is 1: 2.0 to 1: 2.4, optimum proportion is 1: 2.1.
5. a compound method as claimed in claim 3 is characterized in that 1,2,3,4,5,6,7,8-tetrahydrochysene-1, and 5-amerantrone amount of substance (mmol) and polyphosphoric acid volume (mL) are than being 1: 1.5 to 1: 2.5, optimum proportion is 1: 2; 1,2,3,4,5,6,7,8-tetrahydrochysene-1,5-amerantrone amount of substance (mmol) with meta-cresol volume (mL) than being 1: 10 to 1: 20, optimum proportion is 1: 15.
6. a compound method as claimed in claim 3 is characterized in that the reaction times is 40 to 80 hours, and optimum reacting time is 40-60 hour.
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| CN104672211A (en) * | 2015-01-23 | 2015-06-03 | 北京鼎材科技有限公司 | Benzacridine derivatives, and preparation method and applications thereof |
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| CN104193628B (en) * | 2014-08-12 | 2015-11-18 | 李淑兰 | A kind of amino aryl ketone compound and synthetic method thereof being used as medicine intermediate |
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