CN1698137A - 掺杂的有机半导体材料以及其制备方法 - Google Patents
掺杂的有机半导体材料以及其制备方法 Download PDFInfo
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- CN1698137A CN1698137A CNA038009951A CN03800995A CN1698137A CN 1698137 A CN1698137 A CN 1698137A CN A038009951 A CNA038009951 A CN A038009951A CN 03800995 A CN03800995 A CN 03800995A CN 1698137 A CN1698137 A CN 1698137A
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- semiconductor material
- organic semiconductor
- amido
- doped organic
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 64
- 239000000463 material Substances 0.000 title claims abstract description 62
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- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 230000000694 effects Effects 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- -1 methoxyl group Chemical group 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 239000000049 pigment Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 27
- 239000010410 layer Substances 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
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- 239000001301 oxygen Substances 0.000 claims description 24
- 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 claims description 23
- 238000005336 cracking Methods 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
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- 239000000460 chlorine Substances 0.000 claims description 19
- 239000011630 iodine Substances 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
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- 239000004305 biphenyl Substances 0.000 claims description 18
- 235000010290 biphenyl Nutrition 0.000 claims description 18
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
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- 239000011737 fluorine Substances 0.000 claims description 18
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
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- CXZRDVVUVDYSCQ-UHFFFAOYSA-M pyronin B Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3C=C21 CXZRDVVUVDYSCQ-UHFFFAOYSA-M 0.000 claims description 9
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- 150000001768 cations Chemical class 0.000 claims description 6
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
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- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 3
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 3
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 15
- 230000008030 elimination Effects 0.000 claims 15
- 238000003379 elimination reaction Methods 0.000 claims 15
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 229910052710 silicon Inorganic materials 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 239000005864 Sulphur Substances 0.000 claims 4
- 150000004985 diamines Chemical class 0.000 claims 3
- 229910052732 germanium Inorganic materials 0.000 claims 3
- 229910052745 lead Inorganic materials 0.000 claims 3
- 229910052718 tin Inorganic materials 0.000 claims 3
- YOHIALXJJVJDGU-UHFFFAOYSA-N 1h-pyrazole-5-sulfonic acid Chemical class OS(=O)(=O)C1=CC=NN1 YOHIALXJJVJDGU-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- ZIQCCIAIROIHHR-UHFFFAOYSA-N benzene;boric acid Chemical compound OB(O)O.C1=CC=CC=C1 ZIQCCIAIROIHHR-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 150000003732 xanthenes Chemical class 0.000 claims 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- LQVYCDPEZPBOMT-UHFFFAOYSA-N 4-[4-(diethylamino)benzenecarboximidoyl]-n,n-diethylaniline;hydrochloride Chemical compound Cl.C1=CC(N(CC)CC)=CC=C1C(=N)C1=CC=C(N(CC)CC)C=C1 LQVYCDPEZPBOMT-UHFFFAOYSA-N 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
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- JUQPZRLQQYSMEQ-UHFFFAOYSA-N CI Basic red 9 Chemical compound [Cl-].C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)=C1C=CC(=[NH2+])C=C1 JUQPZRLQQYSMEQ-UHFFFAOYSA-N 0.000 claims 1
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- CNYGFPPAGUCRIC-UHFFFAOYSA-L [4-[[4-(dimethylamino)phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;2-hydroxy-2-oxoacetate;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C([O-])=O.OC(=O)C([O-])=O.C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1.C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 CNYGFPPAGUCRIC-UHFFFAOYSA-L 0.000 claims 1
- IURGIPVDZKDLIX-UHFFFAOYSA-M [7-(diethylamino)phenoxazin-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3N=C21 IURGIPVDZKDLIX-UHFFFAOYSA-M 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
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- 125000000382 plumbyl group Chemical group [H][Pb]([H])([H])* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- CVAVMIODJQHEEH-UHFFFAOYSA-O rhodamine B(1+) Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O CVAVMIODJQHEEH-UHFFFAOYSA-O 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一具有提高载流子密度和更高效载流子迁移率的掺杂有机半导体材料,它是通过一有机半导体材料采用由一个或多个有机分子基团A和至少一其他的化合物伴体B组成的化合物的掺杂来获得,这里通过至少一个有机分子基团A的化合物或通过至少一个分子基团A和一其他原子或分子的反应产物,经分解后得到至少一个有机分子基团A来完成所期望的掺杂效果。并叙述了一制备方法。
Description
说明
本发明涉及一按照权利要求1的具有提高载流子密度和更高效载流子迁移率的掺杂的有机半导体材料,以及一按照权利要求48的该掺杂有机半导体的制备方法及该半导体的应用。
自从有机发光二极管和太阳能电池1989出现以来[C.W.Tang et al.,Appl.Phys.Lett.51(12),913(1987)]对得自于有机薄层构成的元件进行了深入的研究。这种膜层对所述的应用而言具有有益的特性,例如对有机发光二极管来说高效的电致发光,对有机太阳能电池的可见光区间具有高的吸收系数,对简单电子电路而言材料和元件的制备是廉价的,以及在商业上可将该有机发光二极管用于显示器。
此外该(光-)电子多层元件的功率标志可通过载流子传递层的能力来确定。在发光二极管的情况下运行时的电荷传递层的欧姆损耗与传导率互相有关,其一方面对所需的运行电压产生直接影响,另一方面还决定着元件的热负荷。另外与有机层载流子浓度的关联会在金属接触点附近发生一带弯曲,其使得载流子的注入变得简便和由此可降低接触阻力。相似的故虑对有机太阳能电池也可得出这样的结论,其效能取决于载流子的传递特性。
通过采用一适合的受主材料对空穴传递层(p-掺杂)和采用一施主材料对电子传递层(n-掺杂)的掺杂可显著提高在有机固体(和由此的传导率)中载流子的密度。除此之外还可期望无机半导体类似经验的应用,这正是基于在一元件中p-和n-掺杂层的应用而不考虑其它因素。在US 5,093,689中叙述了该掺杂载流子传递层(借助受主分子混合的空穴传递层的p-掺杂,借助施主分子混合的电子传递层的n-掺杂)在有机发光二极管中的应用。
下述是迄今为止已知的用于有机汽化层传导率改善的措施:
1.载流子迁移率的提高通过
a)应用有机基团作电子传递层(US 5,811,833),
b)高度整齐排列层的制备,其容许pi-分子运行轨道达到最佳化重叠,
2.可迁移的载流子密度的提高通过
a)对材料的净化和小心翼翼的处理,以避免形成载流子晶格缺陷,
b)借助有机层的掺杂
aa)无机材料(气体,碱金属原子美国专利US 6,013,348(J.Kido etal.);J.Kido et al.,Appl.Phys.Lett.73,2866(1998)),
bb)有机材料(TNCQ(M.Maitrot et al.,J.Appl.Phys.,60(7),2396-2400(1986)),F4TCNQ(M.Pfeiffer et al.,Appl Phys.Lett.73(22),3202(1998)),BEDT-TTF(A.Nollau et al.,J.Appl.Phys.,87(9),4340(2000)))
掺杂的有机载流子层已成功地应用于改良有机发光二极管。通过采用受主材料F4TCNQ对空穴传递层的掺杂,可使发光二极管的运行电压明显降低(X.Zhou et al.,Appl.Phys.Lett.,78(4),410(2001).)。通过采用Cs或Li对电子传递层的掺杂可获得类似的效果(J.Kido et al.,Appl.Phys.Lett.,73(20),2866(1998);J.-S.Huang et al.,Appl.Phys.Lett.,80,139(2002))。
采用无机材料的电子掺杂存在的不足是所用的原子以及分子由于其较小尺寸的原因很容易在元件中发生扩散和由此使得特定的制备如从p-掺杂至n-掺杂区域的清晰过渡变得困难。与此相对,大的有机分子作为掺杂物扩散只起着无关紧要的作用。但是其在现实状况下却有消极的作用,因为潜在的掺杂分子必须以p-掺杂的电子亲和性以及n-掺杂的电离电位的极限值为特征。随之而来则出现分子化学稳定性的下降。
本发明的任务是,给出一克服所述高效掺杂分子的化学不稳定性以及掺杂层制备的解决方案。
按本发明该任务按照权利要求书1所述的特征获得解决。优选的的方案如其他的权利要求。
另外该任务还将按照权利要求书48所述特征的方法来解决。优选的工艺方法的变更如其他的权利要求。
在本发明中使用的有机分子,其在中性条件下虽然不稳定,但是作为带电荷的阳离子或阴离子和在一带有共价化合物配体的化合物中是稳定的。该带电荷的分子可由一先导化合物经原位制备,该化合物可在汽化过程前,过程中或之后被转换成所期望的带电荷的分子。对此无限制,例如一这样的化合物可以是一有机盐或一金属配合物。另外该不稳定掺杂物也可原位由一稳定的先导物质来制备。
迄今为止该所应用的掺杂分子是在中性条件下被加入到掺杂层中的,以在电荷传递至基质上后还存在阴或阳离子。由此中性分子的应用仅是一电荷传递的中间步骤。而按照本发明与此相关的,已叙述过的稳定性问题可借助一已电离的,稳定的分子作为掺杂物来避免。
需要的话,为促进先导化合物的分解还可采用其他的工艺方法。其可为化合物的分裂提供所需的能量,或促使与先导化合物中不需要的基团产生化学反应,使其达不到膜层中,或者从膜层中可容易除去,或该膜层的电子特性不被损害。一按照本发明优选的解决方案例如采用激光使若丹明B氯化物汽化,主要用于生产若丹明B阳离子产品。
如果迄今为止的叙述适用于按照权利要求1将一已带电荷的分子基团分解出来时,那么,当首先从化合物中按照权利要求1产生出一个在原位足够稳定的中性基团,以使其进入膜层组成时则本发明的目的也就达到,该基团在膜层中会发生将基团电子传递至基质以及接受来自基质的其他电子。
在US 5,811,833中,叙述了由一游离基团,特别是五芳基环戊二烯基组成的电子传递层用于有机发光二极管。在US 5,922,396中指出,可制备一来自于金属的有机化合物,特别是来自于十苯基锗茂(-gemanocen)或十苯基铅茂(-plumbocen)这样的膜层(s.a.M.J.Heeg,J.Organometallic Chem.,346,321(1988))。US 5,811,833和US 5,922,396是具有提高的显微载流子迁移率(即在电子跃动过程中的传递速率),因为一带负电荷的五苯基环戊二烯基-分子具有芳香族的特性,和因此借助于所参与分子苯基Pi-电子运行轨道的重叠,使得该在相邻的中性五苯基环戊二烯基-分子上的电子传递得以改善。该传导率的提高可通过一显微载流子迁移率(即在电子跃动过程中的传递速率)的提高来达到。与此相反按照本发明为提高传导率,平衡载流子密度将被提高。例如可通过飞行时间(Time-of-Flight)(载流子迁移率的测定),塞贝克-效率(Seebeck-Effekt)或场效应(载流子密度的测定)来进行鉴别。
另外本发明涉及一为达到另一目在含有其他添加材料的混合膜层中掺杂分子的应用。该目的例如可涉及膜层增长的变化,互相穿插格栅的制备(C.J.Brabec et al.,Adv.Mater.,11(1),15(2001)),或在有机发光二极管中光发射量子效率的改良或借助添加一发光色素而改变发射光的颜色。
另外本发明的意义是,通过对所用掺杂分子进行适当的选择,借助往膜层中添加掺杂分子就已达到这样的目的。例如阳离子色素如若丹明B经常可产生一高的发光量子产率,故可在有机LED(发光二极管)中用作发光色素。
最后本发明还包括添加按权利要求1的分子用在聚合物膜层的掺杂。该膜层通常是借助旋转涂布法通过溶液的沉积来制备的。与已知的电化学掺杂不同,此时该盐的阴离子和阳离子通过所施加的电压被拖拽至相应的触点,因此是可迁移的,相应于权利要求1所给出的本发明聚合物层可用大的,不移动的分子进行掺杂。
为展示本发明在实施实例中采用色素分子若丹明B氯化物作为掺杂物。这里制备了一按照比例(150∶1)的萘四甲酸二酐(NTCDA)和若丹明B的混合层,在室温下得出一le-5S/cm的传导率,其相对于一纯的NTCDA-层而言增加了4个数量级。该物理学的解释是,若丹明B氯化物-分子在比色皿加热过程中分解成了带正电荷的若丹明B分子和带负电荷的氯化物-离子。在混合层中嵌入了该带电荷的若丹明B分子。由于该NTCDA的电子亲和性高于若丹明B的亲和性,为保持总膜层呈电荷中性,所需的电子保持在NTCDA-分子上(3.2eV,H.Meier,“Organic Semiconductors”,Verlag Chemie Weinheim,1974,S.425)。该电子将填充NTCDA的最低的未被占据的运行轨道和由此提高其传导率。该升高的载流子的密度例如可通过测量塞贝克(Seebeck)系数和场效应来确定。对一NTCDA用若丹明B掺杂(50∶1)样品的场效应的测定,证实作为多数载流子所存在的电子浓度为1017cm-3。同样该系统的塞贝克测定遵循n-传导,具有一-1,1mV/K的塞贝克系数,从而使载流子浓度大于迄今为止掺杂NTCDA可达到的浓度(A.Nollau et al.,J.Appl.Phys.,87(9),4340(2000))。
人们用较高的基片温度由C60(富勒烯)借助若丹明B(50∶1)的掺杂制备的膜层,具有6e-3S/cm的传导率。其较在室温下所制备的样品(5e-5S/cm)具有2个数量级的升高。该在汽化时所提供的热量将强化若丹明B的分解。
若丹明B对MePTCDI(苝)-3,4,9,10-四羧酸-N’,N’-二甲基-二酰亚胺)和PTCDA(3,4,9,10-苝-四羧酸二酐)基质的掺杂作用已被证实,与基质的实际化学结构无关。
一已知的有机施主,四硫代富瓦烯(TTF),相对于SCE(Y.Misakiet al.,Adv.Mater.8,804(1996))具有一+0.35V的氧化势能。较强的施主,即具有较小氧化势能的掺杂物在空气中是不稳定的(G.C.Papavassiliou,A.Terzis,P.Delhaes,in:H.S.Nalwa(Ed.)Handbook ofconductive molecules and polymers,Vol.1:charge-transfer salts,fullerenes and photoconductors,John Wiley&Sons,Chichester,1997)。若丹明B相对于NHE(M.S.Chan,J.R.Bolton,Solar Energy,24,561(1980))具有一-0.545V的还原势能,即相对于SCE为-0.79V。若丹明B有机盐的还原势能是由若丹明B阳离子的还原势能决定的。该值与中性若丹明B-基团的氧化势能相同。因此该若丹明B-基团与TTF相比是更强的施主。在若丹明B氯化物的化合物中该强烈的施主却是稳定的。相对于迄今为止可使用具有高于SCE+0.35V的氧化势能的施主而言,这里所述的发明容许用氧化势能小于SCE+0.35V的施主进行掺杂。
按照权利要求1所述的化学稳定的化合物例如可为离子型色素。其在照相业中被用作感光剂如AgBr。该AgBr电子亲合性是3.5eV。借助电子传递可感应AgBr的色素同样适合作为按照权利要求1的用于有机半导体材料掺杂的化学稳定化合物。
一离子型的色素可为二-和三苯基甲烷色素和其已知通用结构的类似物(T1以及T2)
这里X是CR4,SiR4,GeR4,SnR4,PbR4,N,P,而R1,R2,R3和R4为适合的已知的取代物,例如可各是一个或多个;氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
往往在苯基上有一个或多个对位上的取代物(T3至T6)。
这里X是CR8,SiR8,GeR8,SnR8,PbR8,N,P而R1至R7和R8为适合的已知的取代物,例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基,胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基,烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
二苯基甲烷色素的实例为金胺O(CI 655)或金胺G(CI 656)。三苯基甲烷色素的实例为孔雀绿(CI 657),土耳其蓝(CI 661),荧光素(CI 45350)或专利兰V(CI 712)。
三苯基甲烷色素的代表孔雀绿氯化物在NTCDA基质中以掺杂比1∶122可产生一4·10-4S/cm的传导率。孔雀绿也是权利要求11中的化合物和特别适合于其他权利要求12至22,可原位制备出一掺杂分子。该特性是通过中心碳原子(第4主族)的化合价结构引起的。其它含有第4主族原子结构类型的已知化合物(三芳基甲硅烷基,甲锗烷基,甲锡烷基,铅烷基)同样适合于作为权利要求1,12至22的化合物。权利要求23至25包括在二-或三苯基胺的相应苯环的2个碳原子间存在直接键合的化合物。
应用隐色形态的离子型色素(T7 T8)也可产生掺杂作用。若丹明B碱可对一PTCDA基质进行掺杂,例如一1∶70的掺杂可产生7*10-5S/cm的传导率。
一其他的离子型色素基团是呫吨(Xanthen)色素。
上述的若丹明B是该类别的代表。焦宁B,若丹明110和若丹明3B作为该材料种类的另外代表,同样也具有掺杂作用。与呫吨色素类似的还有吡喃-,硫代吡喃-,吲达胺-,丫啶-,丫嗪-,噁嗪-,和噻嗪色素,它们在多核的杂环中通过不同的取代基来区别。此外根据相同的结构,色素组(T9)同样适合于用作权利要求1,23至26的化合物。
基于多次甲基-结构的色素同样可作为掺杂物。
N,N’-二乙基-菁蓝和N,N’-二乙基-硫代碳菁能使-NTCDA基质的传导率提高至3·10-5S/cm(1∶114掺杂比)和5·10-5S/cm(1∶47掺杂比)。这两种色素是具有一定X和Z选择的多次甲基-色素的代表。
离子型色素的隐色碱同样是满足权利要求1,12至26的合适的化合物。例如在NTCDA中若丹明B碱具有3·10-5S/cm(1∶70掺杂比)的传导率。
由于该掺杂作用与离子型色素的色素特性无关,而更多的是与其作为有机盐的特性有关,因此其他有机盐同样可作为权利要求11的化合物。有机盐通常为合适的杂环(例如吡啶嗡(Pyridinium),吡咯嗡(Pyrrolium),吡喃嗡(Pyrylium),噻唑嗡(Thiazolium),二嗪嗡(Diazininium),Thininium,吡唑嗡(Diazolium)或二硫代嗡(Dithiolium)等单独或一个多核杂环的部分)或合适的基团(例如铵,锍,磷嗡,碘嗡等)。
对焦宁B氯化物的质谱研究显示,在焦宁B汽化条件下除HCl外还产生一具有质量数为324的焦宁B的质子化形态。显然它是焦宁B氯化物裂解产生的氯游离基和中性的通过一个质子中和的焦宁B-基团。这些质子是由在汽化物质中的其他焦宁B分子所提供的。由汽化焦宁B氯化物形成的膜层先是无色的。这表明生成的是中性焦宁的形态。在氧的影响下该汽化层可重新变成红色,其与焦宁B的阳离子形态相适应,即该汽化的物质在氧影响下被氧化了。该过程在基质和掺杂物混合层中同样存在。来自于焦宁B氯化物和四氰基奎诺二甲烷的汽化混合层会立刻被染成红色,四氰基奎诺二甲烷阴离子的存在可通过UV/VIS和FTIR分光仪来证实。
Claims (70)
1.具有提高载流子密度和更高效载流子迁移率的掺杂的有机半导体材料是通过一有机半导体材料采用由一或多个有机分子基团A和至少一个其他的化合物伴体B组成的化学化合物的掺杂来获得,这里通过至少一个有机分子基团A的化合物或通过至少一个分子基团A和一其他原子或分子的反应产物,经裂解后得到至少一个有机分子基团A来完成所期望的掺杂效果。
2.按照权利要求1之一的掺杂有机半导体材料,在其中至少另外的化合物伴体B中之一是与A的分子基团相同。
3.按照权利要求1至2之一的掺杂有机半导体材料,在其中该另外的化合物伴体B是一分子基团,一原子或一离子。
4.按照权利要求1至3之一的掺杂有机半导体材料,在其中化合物中的分子基团A是带有单一或多个电荷的阳离子或阴离子。
5.按照权利要求1至4之一的掺杂有机半导体材料,在其中分子基团A由一个或多个吡啶嗡单元产生。
6.按照权利要求5的掺杂有机半导体材料,在其中一个或多个吡啶嗡单元是单核或多核的杂环的一部分。
7.按照权利要求5和6之一的掺杂有机半导体材料,在其中该分子基团A来自于
结构,这里R1,R2,R3和R4例如可各为一个或多个:氢,氧,卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基,磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
8.按照权利要求1至4之一的掺杂有机半导体材料,在其中该分子基团A由一个或多个吡咯嗡-,吡喃嗡盐-,噻唑嗡-,二嗪嗡-,Thininium-,吡唑嗡-,硫代吡唑嗡-,四唑嗡-或二硫代嗡(Dithilim)单元产生。
9.按照权利要求5的掺杂有机半导体材料,在其中一个或多个吡咯嗡-,吡喃嗡盐-,二嗪嗡-,Thininium-,吡唑嗡-,噻唑嗡-,硫代吡唑嗡-,四唑氮嗡-或二硫代嗡单元作为一个或多个多核杂环的部分。
10.按照权利要求1至4之一的掺杂有机半导体材料,在其中分子基团A由一个或多个硼酸苯(Boratabenzen)单元产生。
11.按照权利要求10的掺杂有机半导体材料,在其中一个或多个硼酸苯(Boratabenzen)单元作为一或多个多核杂环的部分。
12.按照权利要求1至11之一的掺杂有机半导体材料,在其中分子基团A是一阳离子的色素,一阴离子的色素或一其它有机盐。
13.按照权利要求1至12之一的掺杂有机半导体材料,在其中分子基团A由结构A1或相应的无色碱A2
产生,这里
X是CR4,SiR4,GeR4,SnR4,PbR4,N,P而R1,R2,R3和R4例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上生成缩合有环的那些原子。
14.按照权利要求1至13之一的掺杂有机半导体材料,在其中该分子基团A由结构A3或相应的无色碱A4
产生,这里
X是CR8,SiR8,GeR8,SnR8,PbR8,N,P而R1,R2,R3,R4,R5,R6,R7,R8例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合生成环的那些原子。
16.按照权利要求1至15之一的掺杂有机半导体材料,在其中分子基团A由结构A7或相应的无色碱A8
产生,这里
X是C,Si,Ge,Sn,Pb,S而R1,R2,R3和R4例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
17.按照权利要求1至16之一的掺杂有机半导体材料,在其中分子基团A由结构A9或相应的无色碱A10
产生,这里
X是C,Si,Ge,Sn,Pb而R1,R2,R3,R4,R5,R6,R7和R8例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
18.按照权利要求1至17之一的掺杂有机半导体材料,在其中分子基团A由结构A11或相应的无色碱A12
产生,这里
X是C,Si,Ge,Sn,Pb而R1,R2,R3,R4例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
19.按照权利要求11至18之一的掺杂有机半导体材料,在其中该化学稳定的化合物是C.I.Basic Yellow 37(C.I.41001)或一其它的带有已知反阴离子(Gegenanion)的二苯基甲烷色素。
20.按照权利要求11至18之一的掺杂有机半导体材料,在其中该化学稳定的化合物是C.I.Basic Green 4(C.I.42000)或一其它的带有已知反阴离子(Gegenanion)的三苯基甲烷色素的二胺衍生物。
21.按照权利要求11至18之一的掺杂有机半导体材料,在其中该化学稳定的化合物是C.I.Basic Red 9(C.I.42500)或一其它的带有已知反阴离子(Gegenanion)的三苯基甲烷色素的三胺衍生物。
22.按照权利要求11至18之一的掺杂有机半导体材料,在其中该化学稳定的化合物是亚苯基兰(C.I.49400)或一其它的带有已知反阴离子(Gegenanion)的吲达胺色素。
27.按照权利要求23至26之一的掺杂有机半导体材料,在其中X是
R例如是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那结原子。
28.按照权利要求11至27之一的掺杂有机半导体材料,在其中该化学稳定的化合物是焦宁B(C.I.45010),C.I.Basic Red 11(C.I.45050),Saccharein(C.I.45070),Rosamine(C.I.45090),若丹明B(C.I.45175)或一其它的带有已知反阴离子的占吨(Xanthen)色素的二胺衍生物。
29.按照权利要求11至27之一的掺杂有机半导体材料,在其中该化学稳定的化合物是Coerulein B(C.I.45500)或一其它的带有已知反阴离子的占吨(Xanthen)色素的二羟基衍生物。
30.按照权利要求11至27之一的掺杂有机半导体材料,在其中该化学稳定的化合物是丫啶黄素(C.I.46000)或一其它的带有已知反阴离子的丫啶的二胺衍生物。
31.按照权利要求11至27之一的掺杂有机半导体材料,在其中该化学稳定的化合物是酚臧花红(C.I.50200)或一其它的带有已知反阴离子的丫嗪色素。
32.按照权利要求11至27之一的掺杂有机半导体材料,在其中该化学稳定的化合物是C.I.Basic Blue 3(C.I.51004)或一其它的带有已知反阴离子的噁嗪色素。
33.按照权利要求11至27之一的掺杂有机半导体材料,在其中该化学稳定的化合物是劳氏紫(C.I.52000)或一其它的带有已知反阴离子的噻嗪色素。
34.按照权利要求11至12之一的掺杂有机半导体材料,在其中分子基团A由结构
产生,这里
n是一自然数,
X和Z各是NR1,S或BR2作为一单核或多核杂环的杂原子,
Xn可为N或CR3而
R1,R2,R3,Rn例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
35.按照权利要求34的掺杂有机半导体材料,在其中X和Z各自由下述基团的一个基元
产生,这里
X1是CR4R5,NR6,O或S而
R1,R2,R3,R4,R5,R6例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
36.按照权利要求11至35之一的掺杂有机半导体材料,在其中该化学稳定的化合物是N,N’-二烷基菁蓝或N,N‘-二烷基硫代碳菁或一其它的带有已知反阴离子的次甲基-或多次甲基色素。
38.按照权利要求11至12之一的掺杂有机半导体材料,在其中分子基团A由结构
产生,这里
X,X1,Z和Z1各为S或Se而
R例如可各是一个或多个:氢;氧;卤素,例如氟,氯,溴或碘;羟基;胺基,例如二苯基胺基,二乙基胺基;具有1至20个碳原子的脂肪烃基,例如甲基,乙基,羧基;烷氧基,例如甲氧基;氰基;硝基;磺酸和其盐;具有3至25个碳原子的芳香基,例如苯基,吡啶基或萘基或在其上缩合成环的那些原子。
41.按照权利要求1至40之一的掺杂有机半导体材料,在其中该化合物含有形式上带正电荷的氮(氮嗡杂,铵),氧(氧嗡杂(oxonia),氧嗡),磷(磷嗡杂,磷嗡),硫(硫嗡杂,硫嗡)和/或形式上带负电荷的硼(boranuida,硼酸盐)。
42.按照权利要求1至41之一的掺杂有机半导体材料,在其中该化合物是一金属配位化合物。
44.按照权利要求1至43之一的掺杂有机半导体材料,在其中一个或多个分子基团A含有一个或多个-SO3 -基团。
45.按照权利要求1至43之一的掺杂有机半导体材料,在其中一个或多个分子基团A含有一个或多个铵-,Immonium-,硫嗡-,肼嗡(Hydrazinium)-或硫脲嗡(Thiouronium)基团。
46.按照权利要求1至42之一的掺杂有机半导体材料,在其中来自于一有机化合物分子A和一分子B的配合物具有这样的性质,即对所希望的多数载流子而言B不会在需掺杂的基质中形成陷阱。
47.按照权利要求1至46之一的掺杂有机半导体材料,在其中用于掺杂的半导体材料本身就是一混合物。
48.具有提高载流子密度和更高效载流子迁移率的掺杂的有机半导体材料的制备方法,其特征是,将一具有至少一其他化合物伴体B的一个或多个有机分子基团A的化合物,借助在真空或惰性的大气压力下的汽化,或者借助与该有机半导体的同时汽化或者借助前后次序的汽化和紧接着发生掺杂物的渗入沉积,这里该所期望的掺杂效果是通过至少一分子基团A的化合物或,通过化合物伴体A与其他原子或分子的反应产物裂解出的至少一个有抗分子基团A来实现的。
49.按照权利要求48的方法,其特征是,化合物裂解为成分A和B是在进入掺杂半导体之后发生的。
50.按照权利要求48和49的方法,其特征是,化合物在制备层中的裂解和/或由制备层中消除成分B获得促进。
51.按照权利要求48至50之一的方法,其特征是,借助引入热量促进该化合物的裂解和/或成分B的消除。
52.按照权利要求48至50之一的方法,其特征是,借助在膜层吸收区间内的光感应促进该化合物的裂解和/或成分B的消除。
53.按照权利要求48至50之一的方法,其特征是,借助具有分子或原子氧或氧离子或分子或原子氢或氢离子的膜层曝光对该化合物的裂解和/或成分B的消除进行促进。
54.按照权利要求48至50之一的方法,其特征是,借助引入一其它的反应伴体,它在膜层中与成分B进行反应生成的反应产物易挥发,从而促进该化学化合物的裂解和/或成分B的消除。
55.按照权利要求48至50之一的方法,其特征是,通过在膜层中的成分B与一第三种材料或基质的一分子反应,反应产物生成一所需多数载流子的Anti-trap或该产物容易从膜层中除去。
56.按照权利要求48的方法,其特征是,借助在汽化过程中对化合物在气相中的处理,促进该化合物的裂解和/或成分B的消除。
57.按照权利要求48和56之一的方法,其特征是,借助光学的感应促进该化合物的裂解和/或成分B的消除。
58.按照权利要求48和56之一的方法,其特征是,借助一带电荷的成分B的偏移或通过一电或磁场使带电荷的成分B偏移来促进该化合物的裂解和/或成分B的消除。
59.按照权利要求48和56之一的方法,其特征是,借助在汽化过程时通过一强电场促进该化合物的裂解和/或成分B的消除。
60.按照权利要求48的方法,其特征是,在汽化源稳定的相中对该化学化合物的裂解和/或成分B的消除进行促进。
61.按照权利要求48,56和60之一的方法,其特征是,借助在汽化过程时引入热量促进该化合物的裂解和/或成分B的消除,这里引入的热或是在化合物的固态或液态中或者是在气相中。
62.按照权利要求48和60之一的方法,其特征是,借助光学感应促进该化合物的裂解和/或成分B的消除。
63.按照权利要求48,56和60之一的方法,其特征是,借助蒸汽在反应表面上的吸附和随后的重新解吸促进该化合物的裂解和/或成分B的消除。
64.按照权利要求48,56和60之一的方法,其特征是,借助蒸汽在一催化剂表面上的吸附和随后的重新解吸促进该化合物的裂解和/或成分B的消除。
65.按照权利要求48和60之一的方法,其特征是,借助采用强激光对该化合物的幅射促进该化合物的裂解和/或成分B的消除。
66.按照权利要求48,56和60之一的方法,其特征是,借助在汽化过程时等离子体的作用促进该化合物的裂解和/或成分B的消除。
67.按照权利要求48和60之一的方法,其特征是,该在汽化源中的化合物与一第三种物质反应,生成后一或多个反应产物用于掺杂。
68.按照权利要求48和60之一的方法,其特征是,使汽化源中的化合物与一催化剂进行相互作用。
69.按照权利要求48和60之一的方法,其特征是,借助一合适电极的电化学工艺促进在汽化源中的化合物进行裂解。
70.一具有提高载流子密度和更高效载流子迁移率的掺杂有机半导体材料的应用,该材料是通过一有机半导体材料采用由一或多个有机分子基团A和至少一其他化合物伴体B组成的化合物的掺杂获得的,这里通过一个有机分子基团A的化合物或通过化合物伴体A和一其他原子或分子的反应产物,经裂解分出至少一个有机分子基团A即可获得所期望的掺杂效果,其特征是,该有机半导体材料在有机太阳能电池,在有机发光二极管,在有机场效应晶体管,在集成有机电路和在有机激光器中用作功能层。
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- 2002-02-20 DE DE10207859A patent/DE10207859A1/de not_active Withdrawn
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WO2003070822A2 (de) | 2003-08-28 |
JP2005525696A (ja) | 2005-08-25 |
DE10307125B4 (de) | 2017-06-22 |
KR100679384B1 (ko) | 2007-02-05 |
AU2003229476A1 (en) | 2003-09-09 |
AU2003229476A8 (en) | 2003-09-09 |
DE10207859A1 (de) | 2003-09-04 |
KR20050004768A (ko) | 2005-01-12 |
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