CN1918261A - 具有各种掺杂剂的蒽衍生物主体 - Google Patents
具有各种掺杂剂的蒽衍生物主体 Download PDFInfo
- Publication number
- CN1918261A CN1918261A CNA2005800049318A CN200580004931A CN1918261A CN 1918261 A CN1918261 A CN 1918261A CN A2005800049318 A CNA2005800049318 A CN A2005800049318A CN 200580004931 A CN200580004931 A CN 200580004931A CN 1918261 A CN1918261 A CN 1918261A
- Authority
- CN
- China
- Prior art keywords
- light
- ring
- blue
- naphthyl
- xenyl
- 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
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- 150000001454 anthracenes Chemical class 0.000 title description 7
- 239000000463 material Substances 0.000 claims abstract description 69
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
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- 125000003118 aryl group Chemical group 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 sulphur compound Chemical class 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 18
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 13
- 238000001228 spectrum Methods 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
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- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
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- 238000004020 luminiscence type Methods 0.000 claims 1
- 150000003464 sulfur compounds Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 89
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- 230000005540 biological transmission Effects 0.000 description 25
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 23
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- 239000010405 anode material Substances 0.000 description 6
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- LNDKNSMGUSCVEE-UHFFFAOYSA-N boron;methane Chemical compound [B].C LNDKNSMGUSCVEE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005321 cobalt glass Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- DETIPBLYXBGBDU-UHFFFAOYSA-N fluoranthene perylene Chemical group C1=CC=C2C=CC=C3C4=CC=CC=C4C1=C23.C2=CC=C3C=CC=C1C4=CC=CC5=CC=CC(C2=C31)=C45 DETIPBLYXBGBDU-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UBEMYRQUSQCJGU-UHFFFAOYSA-N n,n-dinaphthalen-1-ylnaphthalen-2-amine Chemical class C1=CC=C2C(N(C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 UBEMYRQUSQCJGU-UHFFFAOYSA-N 0.000 description 1
- VMVGVGMRBKYIGN-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-1-amine Chemical class C1=CC=C2C(NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 VMVGVGMRBKYIGN-UHFFFAOYSA-N 0.000 description 1
- VCKILGHOSVMDPW-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)-1,2-dihydroacenaphthylen-3-amine Chemical group C1=CC(C2=3)=CC=CC=3CCC2=C1N(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 VCKILGHOSVMDPW-UHFFFAOYSA-N 0.000 description 1
- KOHOWJPDSFTMLH-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-2-amine Chemical group C1=CC=CC=C1N(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(C=CC=C2)C2=C1 KOHOWJPDSFTMLH-UHFFFAOYSA-N 0.000 description 1
- XIENSVDGJFYZGF-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)phenanthren-2-amine Chemical group C1=CC=CC=C1N(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1=CC=C2C3=CC=CC=C3C=CC2=C1 XIENSVDGJFYZGF-UHFFFAOYSA-N 0.000 description 1
- UVDPJISGUVBNGR-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)tetracen-2-amine Chemical group C1=CC=CC=C1N(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(C=C2C(C=C3C=CC=CC3=C2)=C2)C2=C1 UVDPJISGUVBNGR-UHFFFAOYSA-N 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Abstract
Description
实施例 | 类型 | 蓝色EML中 的%NPB,nm NBA | 驱动 电压 | 亮度(cd/A) @20mA/cm 2 | CIEx | CIEy | 到50% 亮度的 小时数 @80mA /cm 2 | 到50% 亮度的预 期小时数 @20mA /cm 2 |
1 | 对比 | 9%,-- | 9.88 | 11.39 | 0.35 | 0.33 | 220 | 2500 |
2 | 发明 | 4%,65nm | 11.51 | 10.15 | 0.44 | 0.35 | 1200 | >10,000 |
3 | 发明 | 7%,65nm | 10.93 | 11.05 | 0.38 | 0.36 | 1100 | >10,000 |
4 | 发明 | 10%,65nm | 10.06 | 10.39 | 0.35 | 0.36 | 1100 | >10,000 |
5 | 发明 | 4%,52nm | 10.59 | 10.57 | 0.45 | 0.35 | 1300 | >10,000 |
6 | 发明 | 7%,52nm | 10.00 | 11.06 | 0.40 | 0.35 | 1100 | >10,000 |
7 | 发明 | 10%,52nm | 9.68 | 11.31 | 0.37 | 0.34 | 900 | >10,000 |
实施例 | 类型 | 蓝色EML中 的%NPB, nm NBA | 驱动电压 | 亮度 (cd/A)-@ 20mA/cm 2 | CIEx | CIEy | 到50%亮度 的时间(小 时)@80mA /cm 2 |
8 | 对比 | 10%,-- | 10.5 | 11.9 | 0.35 | 0.33 | 200 |
9 | 发明 | 10%,50nm | 9.39 | 12.29 | 0.39 | 0.33 | 600 |
Claims (35)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/780,436 | 2004-02-17 | ||
US10/780,436 US7252893B2 (en) | 2004-02-17 | 2004-02-17 | Anthracene derivative host having ranges of dopants |
PCT/US2005/003879 WO2005080527A1 (en) | 2004-02-17 | 2005-02-04 | Anthracene derivative host having ranges of dopants |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1918261A true CN1918261A (zh) | 2007-02-21 |
CN1918261B CN1918261B (zh) | 2012-04-04 |
Family
ID=34838592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN2005800049318A Active CN1918261B (zh) | 2004-02-17 | 2005-02-04 | 具有各种掺杂剂的蒽衍生物主体 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7252893B2 (zh) |
JP (2) | JP2007524745A (zh) |
CN (1) | CN1918261B (zh) |
TW (1) | TWI373505B (zh) |
WO (1) | WO2005080527A1 (zh) |
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CN107805494A (zh) * | 2017-10-27 | 2018-03-16 | 广州工程技术职业学院 | 一种由乙炔桥联芴和蒽衍生物蓝光材料及制备方法 |
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Also Published As
Publication number | Publication date |
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TWI373505B (en) | 2012-10-01 |
WO2005080527A1 (en) | 2005-09-01 |
CN1918261B (zh) | 2012-04-04 |
TW200604314A (en) | 2006-02-01 |
JP2007524745A (ja) | 2007-08-30 |
US7252893B2 (en) | 2007-08-07 |
JP5421432B2 (ja) | 2014-02-19 |
JP2012248852A (ja) | 2012-12-13 |
US20050181232A1 (en) | 2005-08-18 |
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