CN1551895A - 包含螺二芴单元的共轭聚合物及其应用 - Google Patents
包含螺二芴单元的共轭聚合物及其应用 Download PDFInfo
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- CN1551895A CN1551895A CNA028173589A CN02817358A CN1551895A CN 1551895 A CN1551895 A CN 1551895A CN A028173589 A CNA028173589 A CN A028173589A CN 02817358 A CN02817358 A CN 02817358A CN 1551895 A CN1551895 A CN 1551895A
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- 150000004292 cyclic ethers Chemical class 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229950004394 ditiocarb Drugs 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical class IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 239000013580 millipore water Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical class C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 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
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000005029 thianthrenes Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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Abstract
Description
聚合中单体的比例[%] | GPC** | 电致发光*** | 粘度**** | |||||||||
聚合物(类型)* | 单体1 | 单体2 | 单体3 | 单体4 | Mw(1000g/mol) | MN(1000g/mol) | λ max[nm] | 最大发光效率[Cd/A] | 在100Cd/m2时的电压[V] | EL颜色 | 在100Cd/m2时的寿命[h] | 凝胶化温度[℃] |
P1(Y) 87.5%S-SY1 12.5%AM1 155 53 465 2.7 4.0 蓝色 800 <0℃P2(S) 50%S-SY2 40%S-SY1 10%AM1 124 39 463 2.8 4.5 蓝色 1250 <0℃P3(S) 50%S-SY2 40%S-US1 10%AM1 101 41 465 2.6 4.5 蓝色 1150 <0℃P4(S) 50%S-SY2 40%S-US2 10%AM1 90 40 470 3.0 4.7 蓝色 1550 10℃P5(S) 50%S-SY2 40%S-US3 10%AM1 115 45 473 3.2 4.2 蓝色 2250 <0℃P6(S) 50%S-SY2 40%S-US4 10%AM1 87 36 472 2.8 4.5 蓝色 1250 <0℃P7(S) 50%S-SY2 40%S-SY3 10%AM1 120 46 467 1.9 5.1 蓝色 610 10℃P8(S) 50%S-SY4 40%S-SY1 10%AM1 110 38 468 1.8 5.3 蓝色 410 15℃P9(S) 50%S-SY2 40%S-SY1 10%AM2 89 30 470 2.2 5.0 蓝色 900 <0℃P10(S) 50%S-SY2 40%S-SY1 10%AM3 83 29 465 1.6 5.8 蓝色 800 <0℃P11(S) 50%S-SY2 40%S-SY1 10%AM1 124 39 463 2.8 4.5 蓝色 1250 <0℃ | ||||||||||||
P12(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-a 98 48 509 6.8 5.8 绿色 3000 <0℃P13(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-b 77 32 516 7.6 4.6 绿色 4300 <0℃P14(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-c 99 29 516 5.9 5.8 绿色 2800 <0℃P15(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-d 110 51 545 6.9 4.7 黄绿 4000 <0℃色P16(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-e 105 37 527 7.7 3.9 绿色 >5000 <0℃P17(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-f 120 48 525 6.0 4.9 绿色 2100 <0℃P18(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-g 29 10 525 3.1 7.1# 绿色 --- ~20℃P19(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-h 91 29 535 6.7 3.8 绿色 >5000 <0℃P20(S) 50%S-SY2 30%S-SY1 20%CH-h 87 36 534 6.1 4.1 绿色 4000 <0℃P21(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-i 124 63 553 6.5 4.8 黄绿 2500 <0℃色P22(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-k 54 20 541 2.2 5.8 黄绿 --- ~5℃色P23(S) 50%S-SY2 30%S-SY1 10%AM1 10%CH-l 111 54 524 5.9 5.1 绿色 1800 <0℃P24(S) 50%S-SY2 20%S-SY1 20%MX-4 10%CH-b 138 56 516 8.8 3.8 绿色 >5000 <0℃ | ||||||||||||
P25(S) 50%S-SY2 30%S-SY1 10%AM1 10%N2S-1 98 37 551 7.1 4.9 黄绿 1600 <0℃色P26(S) 50%S-SY2 30%S-SY1 10%AM1 10%N2O-1 87 39 575 6.2 5.4 黄色 1200 <0℃ |
聚合中单体的比例[%] | GPC** | 电致发光*** | 粘度**** | |||||||||
聚合物(类型)* | 单体1 | 单体2 | 单体3 | 单体4 | Mw(1000g/mol) | MN(1000g/mol) | λmax[nm] | 最大发光效率[Cd/A] | 在100Cd/m2 时的电压[V] | EL颜色 | 在100Cd/m2时的寿命[h] | 凝胶化温度[℃] |
P27(S) 50%S-SY2 10%AM1 35%N2S-1 5%(N2S-1)-T2-Br2 89 40 632 1.5 3.6 红色 >5000 <0℃P28(S) 50%S-SY2 10%AM1 35%N2S-1 5%(N2S-1)-T1-Br2 112 45 597 1.6 4.9 橙红 >5000 <0℃色P29(S) 50%S-SY2 10%AM1 35%N2S-1 5%(CH-b)-T2-Br2 56 20 619 1.5 3.5 红色 >5000 <0℃P30(S) 50%S-SY2 10%AM1 35%N2S-1 5%(CH-b)-T1-Br2 89 45 590 1.9 3.9 橙红 >5000 <0℃色P30(S) 50%S-SY2 10%AM1 35%N2S-1 5%(5)-T2-Br2 120 62 560 3.2 4.9 橙黄 ---- <0℃色P32(S) 50%S-SY2 10%AM1 35%N2S-1 5%(6)-T2-Br2 79 30 575 1.0 6.9 橙黄 ---- <0℃色P33(S) 50%S-SY2 10%MX-1 35%N2S-1 5%(N2S-1)-T2-Br2 117 48 642 1.9 3.0 红色 >5000 <0℃ | ||||||||||||
P34(S) 50%S-SY2 30%S-SY1 10%AM1 10%MX-1 135 53 520 9.8 3.5 绿色 >5000 <0℃P35(S) 50%S-SY2 30%S-SY1 10%AM1 10%MX-2 102 45 475 4.0 4.2 蓝绿 2100 <0℃色P36(S) 50%S-SY2 30%S-SY1 10%AM1 10%MX-3 65 25 460 2.0 4.4 蓝色 1200 <0℃P37(S) 50%S-SY2 30%S-SY1 10%AM1 10%MX-4 128 60 468 3.2 4.0 蓝色 2000 <0℃P38(S) 50%S-SY2 20%S-SY1 10%AM1 20%MX-4 99 39 468 3.2 3.8 蓝色 1900 <0℃P39(Y) 50%S-SY1 10%AM1 10%MX-4 176 76 466 3.3 4.0 蓝色 2500 <0℃P40(S) 50%S-SY2 20%S-SY1 10%AM1 10%MX-4 112 60 517 10.2 3.0 绿色 >5000 <0℃10%CH-bP41(S) 50%S-SY2 20%S-SY1 10%AM1 10%MX-1 122 62 515 11.2 2.9 绿色 >5000 <0℃10%CH-b | ||||||||||||
V1(S) 50%S-SY2 50%S-SY1 142 62 451 0.1 8.9 蓝色 ---- <0℃V2(S) 50%S-SY2 40%S-SY1 10%MX-1 102 60 518 2.1 9.3 绿色 100h <0℃V3(S) 50%S-SY2 25%S-SY1 25%MX-1 99 38 523 2.0 9.2 绿色 80h <0℃ |
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DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
DE19614971A1 (de) * | 1996-04-17 | 1997-10-23 | Hoechst Ag | Polymere mit Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien |
US5763636A (en) | 1995-10-12 | 1998-06-09 | Hoechst Aktiengesellschaft | Polymers containing spiro atoms and methods of using the same as electroluminescence materials |
CN1206254C (zh) * | 1999-02-04 | 2005-06-15 | 陶氏环球技术公司 | 芴共聚物以及由该共聚物制成的器件 |
DE10109027A1 (de) * | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
KR100888910B1 (ko) * | 2001-03-24 | 2009-03-16 | 메르크 파텐트 게엠베하 | 스피로비플루오렌 단위와 플루오렌 단위를 함유하는 공액중합체 및 이의 용도 |
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2002
- 2002-08-29 CN CNA2008101453287A patent/CN101343215A/zh active Pending
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- 2002-08-29 DE DE50209372T patent/DE50209372D1/de not_active Expired - Lifetime
- 2002-08-29 US US10/488,625 patent/US7323533B2/en not_active Expired - Lifetime
- 2002-08-29 EP EP02772227A patent/EP1427768B1/de not_active Expired - Lifetime
- 2002-08-29 KR KR1020047003221A patent/KR100895236B1/ko active IP Right Grant
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1957018B (zh) * | 2004-05-11 | 2011-02-02 | 默克专利有限公司 | 电致发光聚合物 |
CN101146814B (zh) * | 2005-03-01 | 2013-01-02 | 新加坡科技研究局 | 经溶液加工的有机金属配合物及其在电致发光器件中的用途 |
CN101331558B (zh) * | 2005-12-17 | 2012-10-03 | 默克专利有限公司 | 共轭聚合物、其制备和用途 |
CN102076737A (zh) * | 2008-09-25 | 2011-05-25 | 默克专利有限公司 | 具有低多分散性的新型聚合物 |
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CN101343215A (zh) | 2009-01-14 |
WO2003020790A2 (de) | 2003-03-13 |
WO2003020790A3 (de) | 2003-09-12 |
US20070265473A1 (en) | 2007-11-15 |
CN100422236C (zh) | 2008-10-01 |
DE50209372D1 (de) | 2007-03-15 |
EP1427768B1 (de) | 2007-01-24 |
US7323533B2 (en) | 2008-01-29 |
US7638594B2 (en) | 2009-12-29 |
JP2005508401A (ja) | 2005-03-31 |
DE10143353A1 (de) | 2003-03-20 |
KR20040044536A (ko) | 2004-05-28 |
US20050038223A1 (en) | 2005-02-17 |
KR100895236B1 (ko) | 2009-05-04 |
EP1427768A2 (de) | 2004-06-16 |
JP4515091B2 (ja) | 2010-07-28 |
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