CN107721861A - 用于有机电子器件的菲化合物 - Google Patents
用于有机电子器件的菲化合物 Download PDFInfo
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- CN107721861A CN107721861A CN201710958159.8A CN201710958159A CN107721861A CN 107721861 A CN107721861 A CN 107721861A CN 201710958159 A CN201710958159 A CN 201710958159A CN 107721861 A CN107721861 A CN 107721861A
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IBXNCJKFFQIKKY-UHFFFAOYSA-N n-propylacetylene Natural products CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 150000002894 organic compounds Chemical class 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
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 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
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YSZJKUDBYALHQE-UHFFFAOYSA-N rhenium trioxide Chemical compound O=[Re](=O)=O YSZJKUDBYALHQE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium 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
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007921 spray Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
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- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
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- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
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- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/26—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a double bond between positions 10 and 11
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- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
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- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
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- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
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- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
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- C07D311/82—Xanthenes
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Abstract
本发明涉及一种用于有机电子器件的菲化合物。具体地,本发明涉及特定的菲,涉及所述化合物在电子器件中的用途,和涉及包含这些化合物中的至少一种的电子器件。本发明还涉及制备所述化合物的方法,并且涉及包含所述化合物中的一种或多种的制剂和组合物。
Description
本申请是申请日为2013年5月6日、申请号为201380029898.9、发明名称为“用于有机电子器件的菲化合物”的中国发明专利申请的分案申请。
技术领域
本发明涉及一种用于有机电子器件的菲化合物。具体地,本发明涉及一种新型的有机化合物,涉及所述化合物在电子器件中的用途,和涉及包含至少一种所述化合物的电子器件。本发明还涉及制备所述化合物的方法和涉及包含至少一种所述化合物的组合物和制剂。
背景技术
用于电子器件的功能化合物的开发目前是大力研究的主题。此处的目的特别是开发如下的化合物,使用所述化合物能够在一个或多个相关点例如发光的性能效率、寿命或颜色坐标实现电子器件的性质的改进。
根据本发明、术语电子器件特别是被认为是指有机集成电路 (OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-laser)和有机电致发光器件(OLED)。
特别关注的是提供在最后提到的被称为OLED的电子器件中使用的化合物。OLED的一般结构和功能原理对于本领域普通技术人员是已知的,并且特别是描述在US 4539507、US 5151629、EP 0676461和 WO 1998/27136中。
关于OLED的性能数据,进一步的改进仍是需要的,尤其是鉴于广泛的商业使用,例如在显示装置中或作为光源仍然需要改进。在这方面尤其重要的是OLED的寿命、效率和工作电压和实现的色值。此外,期望作为功能材料用于电子器件中的化合物具有高的热稳定性和高的玻璃化转变温度并且能够在不降解的情况下升华。
在这一点上,特别是需要可选的空穴传输材料。在依照现有技术的空穴传输材料的情况下,电压通常随着空穴传输层的层厚度而增加。在实践中,空穴传输层的更大的厚度经常是期望的,但是这通常导致较高的工作电压和较差的性能数据。就此而论,需要具有高电荷-载流子迁移率的新型空穴传输材料,从而可实现工作电压仅稍微增加的较厚的空穴传输层。
现有技术公开了特别是将芳基胺化合物和咔唑化合物用作OLED 的空穴传输材料。
申请WO 2010/083871公开了由一个或多个芳基氨基基团取代的二氢吖啶衍生物用作OLED中的功能材料,优选地用作空穴传输和空穴注入材料。
KR 2011047803公开了可以是二胺或单胺的菲,其中在单胺的情况下该氨基基团不通过菲的3位键合。
JP 1992321649公开了包含两个烯烃基团的芳族叔胺。还公开了呈现为在3位含有氨基基团的菲的单个化合物,其中所述胺另外被两个本身各自含有烯烃基团的芳族基团取代。
US 2008/0182129公开了由芳族胺取代的蒽,其中所述芳族基团也可以是菲。
WO 2011/136482描述了取代的菲作为电荷传输化合物。在此公开的菲至少被二取代,其中两个取代基都含有胺基团。
但是,仍然需要在OLED中使用的新型空穴传输和空穴注入材料。特别地,需要如下的材料,使用该材料能够实现上面提到的在OLED 的性能数据和性质方面非常期望的改进。
同样地需要在OLED中和在其它电子器件中使用新型基质材料。特别地,需要用于磷光掺杂剂的基质材料和用于混合基质体系的基质材料,该基质材料优选地产生电子器件的良好效率、长寿命和低工作电压。
发明内容
本发明因此基于提供如下化合物的目的,所述化合物适合用于电子器件例如OLED中,和特别是能够用作空穴传输材料和/或用作空穴注入材料和/或用作发光材料和/或用作基质材料。
在本发明的情况下,已经令人预料不到地发现,在下文示出的式 (1)化合物非常适合用于上文提到的用途。
本发明因此涉及式(1)的化合物
其中如下适用于使用的符号和标记:
X在每次出现时相同或不同地是N和CR1,其中最多2个X可等于N;
L是单键或具有12至40个环原子的二价的芳基或杂芳基基团,所述芳基或杂芳基基团可被一个或多个基团R2取代,其中,如果L是单键,则氮直接键合至所述菲的3位,其中L优选是单键;
Ar1、Ar2在每次出现时相同或不同地是具有5至40个芳族环原子的芳族或杂芳族环或者芳族或杂芳族环系,其中所述环或环系可被一个或多个基团R4取代,其中,如果Ar1和Ar2均为苯基基团,则在所述苯基基团上的至少一个R4不等于H,和该至少一个基团R4优选地本身含有一个或多个芳族或杂芳族环,其中优选Ar1和Ar2基团中的每个都含有至少两个芳族环或杂芳族环,和其中以形成非芳族或非杂芳族环的方式,所述环可在Ar1中桥连和/或所述环可在Ar2中桥连;其中非常优选所述环不桥连;
R1在每次出现时相同或不同地是H,D,F,Cl,Br,I,C(=O)R2, CN,Si(R2)3,NO2,P(=O)(R2)2,S(=O)R2,S(=O)2R2,具有1至20个 C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至20个C原子的支链或环状烷基、烷氧基或硫代烷基基团或者具有2至20个C原子的烯基或炔基基团,其中上面提到的基团中的每个可被一个或多个基团R2取代,和其中在上面提到的基团中的一个或多个CH2基团可被 -R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、C(=O)O-、-C(=O)NR2-、 P(=O)(R2)、-O-、-S-、SO或SO2代替,和其中在上面提到的基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有6 至30个芳族环原子的芳族环系,所述芳族环系可在每种情况下被一个或多个基团R2取代,其中两个或更多个基团R1可互相地连接和可形成环;
R4在每次出现时相同或不同地是H,D,F,Cl,Br,I,C(=O)R2, CN,Si(R2)3,NR2,NO2,P(=O)(R2)2,S(=O)R2,S(=O)2R2,具有1至20个C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至20个C 原子的支链或环状烷基、烷氧基或硫代烷基基团或者具有2至20个C 原子的烯基或炔基基团,其中上面提到的基团中的每个可被一个或多个基团R2取代,和其中在上面提到的基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、 -C(=O)NR2-、P(=O)(R2)、-O-、-S-、SO或SO2代替,和其中在上面提到的基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有6至30个芳族环原子的芳族环系,所述芳族环系可在每种情况下被一个或多个基团R2取代,其中两个或更多个基团R4可互相地连接和可形成环;
R2在每次出现时相同或不同地是H,D,F,Cl,Br,I,C(=O)R3, CN,Si(R3)3,NO2,P(=O)(R3)2,S(=O)R3,S(=O)2R3,具有1至20个 C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至20个C原子的支链或环状烷基、烷氧基或硫代烷基基团或者具有2至20个C原子的烯基或炔基基团,其中上面提到的基团中的每个可被一个或多个基团R3取代,和其中在上面提到的基团中的一个或多个CH2基团可被 -R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、 P(=O)(R3)、-O-、-S-、SO或SO2代替,和其中在上面提到的基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5 至30个芳族环原子的芳族或杂芳族环系,其可在每种情况下被一个或多个基团R3取代,或具有5至30个芳族环原子的芳氧基或杂芳氧基基团,其可被一个或多个基团R3取代,其中两个或更多个基团R2可互相地连接和可形成环;
R3在每次出现时相同或不同地是H,D,F,或具有1至20个C 原子的脂族的、芳族的或杂芳族的有机基团,其中一个或多个H原子还可被D或F代替;两个或更多个取代基R3在此处可互相地连接和可形成环;
其条件是,除了所述菲以外,式(1)的化合物不包含另外的具有多于10个环原子的稠合的芳族或杂芳族环,和
其条件是,在式(1)中在所述菲上的基团R1不包含另外的胺基团。
菲上的编号在此如下文所限定的。
在本发明意义上的芳基基团含有6至60个芳族环原子;在本发明意义上的杂芳基基团含有5至60个芳族环原子,其中的至少一个是杂原子。该杂原子优选地选自N、O和S。这代表了基本的定义。关于例如存在的芳族环原子或杂原子的数量,如果在本发明的说明书中示出了其它优选,则适用这些优选。
芳基基团或杂芳基基团在此处是指简单的芳族环,即苯,或简单的杂芳族环,例如吡啶、嘧啶或噻吩,或稠合的(缩合的)芳族或杂芳族多环,例如萘、菲、喹啉或咔唑。在本发明意义上的稠合的(缩合的) 芳族或杂芳族多环由两个或更多个互相稠合的简单的芳族或杂芳族环组成。
可在每种情况下被上面提到的基团取代的和通过任何期望的位置连接到所述芳族或杂芳族环系的芳基或杂芳基基团特别是被认为是指衍生自如下物质的基团:苯、萘、蒽、菲、芘、二氢芘、苝、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶,苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4- 噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4- 四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑。
依照本发明的定义的芳氧基基团被认为是指通过氧原子键合的如上所定义的芳基基团。类似的定义适用于杂芳氧基基团。
在本发明意义上的芳族环系在环系中含有6至60个C原子。在本发明意义上的杂芳族环系含有5至60个芳族环原子,其中的至少一个是杂原子。该杂原子优选地选自N、O和/或S。在本发明意义上的芳族或杂芳族环系旨在被认为是指如下的体系,其不必仅含有芳基或杂芳基基团,而是其中多个芳基或杂芳基基团还可通过非芳族单元(优选少于非H外原子的10%)连接,该非芳族单元例如是sp3-杂化的C、 Si、N或O原子,sp2-杂化的C或N原子,或sp-杂化的C原子。因此,例如,和其中两个或更多个芳基基团例如通过直链或环状烷基、烯基或炔基基团或通过甲硅烷基基团连接的体系一样,诸如9,9’-螺二芴、 9,9’-二芳基芴、三芳基胺、二芳基醚、茋等的体系,也旨在被认为是指本发明意义上的芳族环系。另外地,在其中两个或更多个芳基或杂芳基基团通过单键互相连接的体系,例如,诸如联苯、三联苯或二苯基三嗪的体系,也被认为是指在本发明意义上的芳族或杂芳族环系。
还可在每种情况下被上面定义的基团取代的和可通过任何期望的位置连接到芳族或杂芳族基团的具有5-60个芳族环原子的芳族或杂芳族环系,特别是被认为是指衍生自如下物质的基团或这些基团的组合:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯,三聚苯,四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吲哚并咔唑、茚并咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘、4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3- 三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4- 噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4- 四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑。
为了本发明的目的,其中单独的H原子或CH2基团还可被上文所提及在所述基团定义下的基团取代的具有1至40个C原子的直链烷基基团或具有3至40个C原子的支链或环状烷基基团或具有2至40个C 原子的烯基或炔基基团,优选地指如下基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。具有1至40个C原子的烷氧基或硫代烷基基团优选地被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基,乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。
为了本发明的目的,两个或更多个基团可相互形成环的构想特别是旨在被认为是指,两个基团通过化学键相互连接。这通过如下图示进行示例:
另外地,然而,上面提到的构想也旨在被认为是指,在所述两个基团的一个代表氢的情况下,第二个基团在该氢原子键合的位置处键合而形成环。这旨在通过如下图示进行示例:
为了本发明的目的,优选通式(2)的化合物
其中上文的限定适用于所述符号。
为了本发明的目的,非常优选通式(3)的化合物
本发明另外优选的实施方案是通式(4)的化合物,其中所述符号如上文所限定的。
为了本发明的目的,还优选通式(4a)的化合物,其中所述符号如上文所限定的,并且其它地方提到的优选实施方式也适用于式(4a)。因此,例如,在本发明的一种尤其优选的实施方案中,在该式的化合物中的L 是单键,和基团Ar1和Ar2非常特别地优选各含有至少两个芳基或杂芳基基团。
为了本发明的目的,还优选通式(4b)的化合物
其中
Q在每次出现时相同或不同地是CR4或N;
和其中上文的限定和其优选实施方案适用于其它符号。
为了本发明的目的,还优选通式(5)的化合物
其中
Q在每次出现时相同或不同地是CR4或N;
和其中上文的限定和其优选的实施方案适用于其它符号。
在一种非常优选的实施方案中,本发明涉及通式(6)的化合物
其中上文的限定和其优选的实施方案适用于使用的符号和标记。
特别优选通式(7)的化合物
在本发明的另一种非常特别优选的实施方案中,在两个环的每个环中的5个Q中的至少4个等于CR4,非常特别地优选所有的Q等于 CR4。
如已经在上面描述的,除了所述菲以外,式(1)化合物不包含另外的具有多于10个环原子的稠合的芳族或杂芳族环。因此,取代基Ar1和Ar2和环A和B不代表具有多于10个环原子的稠合的芳族或杂芳族环系。
优选在式(1)中基团Ar1和Ar2或A和B的至少一个含有多于一个环,非常优选基团Ar1和Ar2或A和B都含有至少2个或更多个环。
为了本发明的目的,还优选如下的通式(1)化合物,其特征在于含有总共至少26个、非常优选总共至少32个、非常特别地优选总共至少38个和尤其优选总共至少44个环原子。
在本发明的一种特别优选的实施方案中,式(1)至(7)的化合物在与菲直接键合的任何基团R1中不含芳族或杂芳族基团或者芳族或杂芳族环系,其中式(1)至(7)的化合物甚至更优选地仅含有一个胺基团。这产生特别地非常适合用于有机电子器件中和尤其有机电致发光器件中的化合物。
由如下的式(8)至(106)表示作为基团Ar1和Ar2的特别优选的芳族和杂芳族单元:
其中虚线代表键合位置和其中所述结构可由一个或多个基团R4取代,并且R4如上文所限定的。
在一种优选实施方案中,L是选自亚联苯基、亚三联苯基和如下式(101a)和(101b)的化合物的芳族环系
其中Y等于C(R2)2、NR2、O、Si(R2)2和S,优选是C(R2)2、NR2、 O和S,非常优选是C(R2)2、NR2和O,和尤其优选是C(R2)2和NR2,并且其中R2如上文所限定的。
在一种非常优选的实施方案中,L是单键,即,氮原子通过单键直接与菲在3位键合。
在一种尤其优选的实施方案中,本发明涉及如下的式(1)的化合物,其特征在于所述化合物仅含有一个胺基团,以致式(1)的化合物因此是单胺。
在下表中描绘了本发明的化合物的实例。
本发明的化合物可通过现有技术已知的方法和反应类型例如卤化、Buchwald偶联和Suzuki偶联来合成。
用于制备本发明化合物的优选方法开始于在图式1中作为原料描述的基本结构。这些在一些情况下是商业可购买的,在另外的情况下可从简单的、商业可购买的化合物用几个合成步骤来制备。
下面的图示1显示了用于制备本发明化合物的优选的合成步骤。为了合成本发明的化合物,菲化合物A与式Ar2-NH-Ar1的胺B以 Buchwald偶联的方式反应。
图示1
用于制备本发明化合物的另一个优选的合成路径如图示2所描绘的。该反应路径包含两个偶联反应:首先,菲化合物A与式Ar2-NH2的胺C在第一Buchwald偶联中反应。最后,与化合物D,例如与溴代芳基化合物,进行第二Buchwald偶联。
图示2
所述偶联反应在此优选为Buchwald偶联。
起始化合物(A)的合成对于本领域普通技术人员没有困难。它们可例如通过如下方式来制备:乙酰基化合物至胺的转化,接下来是通过Sandmayer反应至卤化物的转化。关于此的实施例在下文中公开。
如上描述的本发明的化合物,尤其是由反应性离去基团例如溴、碘、氯、硼酸或硼酸酯取代的化合物,可用作生产相应的低聚物、树枝状大分子或聚合物的单体。在此的低聚或聚合优选通过卤素官能团或硼酸官能团而发生。
本发明因此还涉及制备式(1)化合物的方法,其特征在于所述方法依照反应式1或依照反应式2实施。
如上描述的本发明的化合物,尤其是由反应性离去基团例如溴、碘、氯、硼酸或硼酸酯取代的化合物,可用作生产相应的低聚物、树枝状大分子或聚合物的单体。合适的反应性离去基团例如是溴,碘,氯,硼酸,硼酸酯,胺,分别含有末端C-C双键或C-C三键的烯基或炔基基团,环氧乙烷,环氧丁烷,经受环加成例如1,3-偶极环加成的基团,例如二烯或叠氮化物,羧酸衍生物,醇和硅烷。
本发明因此还涉及含有一种或多种式(1)化合物的低聚物、聚合物或树枝状大分子,其中形成所述聚合物、低聚物或树枝状大分子的键可位于在式(1)中由R1或R2取代的任何期望的位置处。取决于式(1)的化合物的连接,所述化合物是低聚物或聚合物的侧链的一部分或主链的一部分。在本发明意义上的低聚物被认为是指从至少三个单体单元构建的化合物。在本发明意义上的聚合物被认为是指从至少十个单体单元构建的化合物。本发明的聚合物、低聚物或树枝状大分子可以是共轭的、部分共轭的或非共轭的。本发明的低聚物或聚合物可以是直链的、支链的或树枝状的。在以直链方式连接的结构中,式(1)的单元可互相直接连接或可通过二价基团互相连接,例如通过取代或非取代的烯基基团、通过杂原子或通过二价的芳族或杂芳族基团互相连接。在支链和树枝状的结构中,三个或更多个式(1)的单元可例如通过三价或更多价的基团连接,例如通过三价或更多价的芳族或杂芳族基团连接,以生成支链或树枝状的低聚物或聚合物。
如上对于式(1)化合物所描述的相同优选适用于所述低聚物、树枝状大分子和聚合物的式(1)重复单元。
为了制备所述低聚物或聚合物,使本发明的单体均聚或与另外的单体共聚。合适和优选的共聚单体选自芴(例如依照EP 842208或WO 2000/22026的),螺二芴(例如依照EP707020、EP 894107或WO 2006/061181的),对亚苯基(例如依照WO 1992/18552的),咔唑(例如依照WO 2004/070772或WO 2004/113468的),噻吩(例如依照EP 1028136的),二氢菲(例如依照WO 2005/014689或WO 2007/006383 的),顺式和反式茚并芴(例如依照WO 2004/041901或WO 2004/113412 的),酮(例如依照WO 2005/040302的),菲(例如依照WO 2005/104264 或WO 2007/017066的)或另外多种这些单元。所述聚合物、低聚物和树枝状大分子通常也含有另外的单元,例如发光(荧光或磷光)单元,例如乙烯基三芳基胺(例如依照WO2007/068325的)或磷光金属络合物 (例如依照WO 2006/003000的),和/或电荷传输单元,尤其是基于三芳基胺的电荷传输单元。
本发明的聚合物、低聚物和树枝状大分子具有有利的性质,尤其是长寿命、高效率和好的颜色坐标。
本发明的聚合物和低聚物一般通过一种或多种类型的单体的聚合而制备,其中至少一种单体导致在聚合物中产生式(1)的重复单元。合适的聚合反应对于本领域普通技术人员是已知的并且描述在文献中。尤其适合和优选的产生C-C或C-N连接的聚合反应是如下的:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合;和
(D)HARTWIG-Buchwald聚合。
其中通过这些方法实施聚合并且其中聚合物然后能从反应介质分离和纯化的方式对于本领域普通技术人员是已知的并且在文献中有详细描述,例如在WO 2003/048225、WO 2004/037887和WO 2004/037887 中描述。
本发明因此还涉及用于制备本发明聚合物、低聚物和树枝状大分子的方法,其特征在于它们通过SUZUKI聚合、YAMAMOTO聚合、 STILLE聚合或HARTWIG-Buchwald聚合而制备。本发明的树枝状大分子可通过对于本领域普通技术人员已知的方法或与其类似的方法来制备。合适的方法描述在文献中,例如在Frechet,Jean M.J.;Hawker, Craig J.,“Hyperbranched polyphenylene and hyperbranched polyesters: new soluble,three-dimensional,reactive polymers”(超支化聚亚苯基和超支化聚酯:新型可溶性的三维反应性聚合物),Reactive&Functional Polymers(反应性和功能性聚合物)(1995),26(1-3),127-36;Janssen,H. M.;Meijer,E.W.,“The synthesis and characterization ofdendritic molecules”(树枝状分子的合成和表征),Materials Science and Technology(分子科学和技术)(1999),20(Synthesis of Polymers(聚合物的合成)),403-458;Tomalia,Donald A.,“Dendrimer molecules”(树枝状大分子),Scientific American(科学美国人)(1995),272(5),62-6; WO 2002/067343A1和WO2005/026144A1中。
为了从液相中例如通过旋涂或通过印刷方法加工本发明的化合物,本发明化合物的制剂是必要的。这些制剂可例如是溶液、分散体或微乳液。为此可优选使用两种或更多种溶剂的混合物。适合和优选的溶剂例如是甲苯、苯氧基甲苯、苯甲醚、邻-、间-或对-二甲苯、苯甲酸甲酯,二甲基苯甲醚、均三甲苯、四氢萘、邻二甲氧基苯、THF、甲基-THF、THP、氯苯,二烷或这些溶剂的混合物。
本发明因此还涉及如下的制剂,特别是溶液、分散体或微乳液,其包含至少一种式(1)的化合物或至少一种含有至少一种式(1)单元的聚合物、低聚物或树枝状大分子,和至少一种溶剂,优选有机溶剂。其中能够制备这种类型的溶液的方式对于本领域普通技术人员是已知的并且例如描述在WO 2002/072714、WO 2003/019694和其中所引用的文献中。
可作为与在电子器件中使用的其它有机功能材料的组合物使用本发明的化合物。多种可行的有机功能材料(通常也称作有机半导体) 在此处对本领域普通技术人员是已知的。本发明因此还涉及包含一种或多种本发明化合物和至少一种另外的有机功能材料的组合物,所述至少一种另外的有机功能材料选自荧光发光体、磷光发光体、主体材料、基质材料、电子传输材料、电子注入材料、空穴导体材料 (Lochleitermaterialien)、空穴注入材料、电子阻挡材料和空穴阻挡材料。
本发明的化合物适合用于电子器件中,尤其是有机电致发光器件 (OLED)中。取决于取代,所述化合物在多种功能和层中使用。
本发明因此还涉及式(1)化合物在电子器件中的用途,并且涉及包含一种或多种式(1)化合物的电子器件本身。所述电子器件在此处优选地选自有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-laser),和尤其优选有机电致发光器件 (OLED)。
如已经在上文所陈述的,本发明涉及包含至少一种式(1)化合物的电子器件。所述电子器件在此处优选地选自上面提到的器件。特别优选包含阳极、阴极和至少一个发光层的有机电致发光器件(OLED),其特征在于至少一个有机层包含至少一种式(1)的化合物,所述有机层可以是发光层、空穴传输层或另外的层。
除了阴极、阳极和发光层之外,所述有机电致发光器件还可以包括另外的层。这些层例如在每种情况下选自一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、电子阻挡层、激子阻挡层、中间层、电荷产生层((IDMC 2003,中国台湾;Session 21OLED (5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,Multiphoton Organic EL Device Having Charge Generation Layer (具有电荷产生层的多光子有机EL器件))和/或有机或无机p/n结。然而,应当指出不必须存在这些层中的每个,且层的选择通常取决于使用的化合物以及特别是还取决于所述电致发光器件是发荧光的还是发磷光的。
本发明有机电致发光器件也可以包括多个发光层。在这种情况下,特别优选这些发光层总共具有多个在380nm和750nm之间的发光峰值,导致总体上白色发光,即,将能够发荧光或发磷光且发蓝色或黄色或橙色或红色光的多种发光化合物用于所述发光层中。特别优选三层体系,即具有三个发光层的体系,其中这三个层显示蓝色、绿色和橙色或红色发光(对于基本结构,例如见WO 2005/011013)。本发明的化合物可存在于空穴传输层、发光层和/或在这种器件的其它层中。应该指出,为了产生白光,代替多种以特定颜色发光的发光体化合物,单独使用的在宽的波长范围发光的发光体化合物也是合适的。
根据本发明,优选式(1)的化合物用于包含一种或多种磷光掺杂剂的电子器件中。所述化合物在此可用于多个层中,优选用于空穴传输层、空穴注入层中或用于发光层中。但是,依照本发明,式(1)的化合物也可用于包含一种或多种荧光掺杂剂的电子器件中。
如果式(1)的化合物在空穴传输层、空穴注入层或电子阻挡层中用作空穴传输材料,则所述化合物可作为纯材料,即以100%的比例,用于空穴传输层中,或者它可与一种或多种另外的化合物组合使用。根据一种优选的实施方案,包含式(1)化合物的有机层此外还包含一种或多种p-掺杂剂。依照本发明使用的p-掺杂剂优选为有机电子受体化合物,所述有机电子受体化合物能够氧化混合物的一种或多种的其它化合物。
p-掺杂剂的特别优选的实施方案是在如下文献中公开的化合物: WO 2011/073149、EP 1968131、EP 2276085、EP 2213662、EP 1722602、 EP 2045848、DE102007031220、US 8044390、US 8057712、WO 2009/003455、WO 2010/094378、WO 2011/120709、US 2010/0096600和WO 2012/095143。
在本发明的另外的优选实施方案中,式(1)的化合物用作空穴传输材料,与六氮杂苯并菲衍生物组合,如在US 2007/0092755中所描述的。该六氮杂苯并菲衍生物在此尤其优选用于单独的层中。
尤其优选的p-掺杂剂是醌二甲烷化合物,氮杂茚并芴二酮,氮杂非那烯(Azaphenalene),氮杂苯并菲,I2,金属卤化物,优选过渡金属卤化物,金属氧化物,优选含有至少一种过渡金属或第3主族金属的金属氧化物,和过渡金属络合物,优选Cu、Co、Ni、Pd和Pt与具有含有至少一个氧原子作为键合位点的配体的络合物。另外优选过渡金属氧化物作为掺杂剂,优选铼、钼和钨的氧化物,尤其优选Re2O7、 MoO3、WO3和ReO3。
此外,优选的p-掺杂剂是如下的化合物:
在空穴传输层中的p-掺杂剂优选以如下的浓度存在:按体积计 0.1%至20%,非常优选按体积计0.5%至12%,尤其优选按体积计1%至8%,非常特别优选按体积计2%至6%。
所述空穴传输层优选具有5至50nm的厚度,尤其优选10至40nm 的厚度。
术语磷光掺杂剂通常包括如下的化合物,其中通过自旋禁阻的跃迁而发光,所述自旋禁阻的跃迁例如是从激发三重态或自旋量子数相对高的态例如五重态的跃迁。
合适的磷光掺杂剂(=三重态发光体)特别是如下的化合物,其在合适的激发下优选在可见区域发光,并且另外含有至少一个如下的原子,所述原子的原子序数大于20、优选大于38且小于84、尤其优选大于 56且小于80。使用的磷光发光体优选是含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是含有铱、钯或铜的化合物。
所有发光的铱、钯或铜络合物都被视为在本发明的意义上的磷光化合物。
申请WO 00/70655、WO 01/41512、WO 02/02714、WO 02/15645、 EP 1191613、EP1191612、EP 1191614、WO 2005/033244、WO 2005/019373和US 2005/0258742,公开了上文所述发光体的实例。通常,根据现有技术用于磷光OLED的和在有机电致发光器件领域中为本领域普通技术人员所已知的所有磷光络合物都是合适的。本领域普通技术人员也将能够在不付出创造性劳动的情况下将式(1)化合物与另外的磷光络合物组合用于有机电致发光器件中。
此外,通过下表公开了合适的磷光发光体化合物的明确的实例。
在本发明的一种优选实施方案中,式(1)化合物用作空穴传输材料。那么所述化合物优选用于空穴传输层和/或空穴注入层中。空穴注入层在本发明意义上是直接与阳极相邻的层。空穴传输层在本发明意义上是位于空穴注入层和发光层之间的层。空穴传输层可以直接与发光层相邻。如果式(1)化合物用作空穴传输材料或空穴注入材料,则可优选其掺杂有电子受体化合物,例如掺杂有F4-TCNQ或掺杂有在EP 1476881或EP 1596445中描述的化合物。在本发明的一种另外的优选实施方案中,式(I)的化合物用作空穴传输材料,与六氮杂苯并菲衍生物组合,如在US 2007/0092755中所描述的。在此六氮杂苯并菲衍生物尤其优选用于单独的层中。
如果式(1)化合物在空穴传输层中用作空穴传输材料,则所述化合物可以以纯材料即100%的比例用于空穴传输层,或者它可与一种或多种另外的化合物组合用于空穴传输层中。
在本发明的一种另外的实施方案中,式(1)化合物用作发光材料。为此,所述化合物优选地用于发光层中。除至少一种式(1)的化合物外,所述发光层还包含至少一种主体材料。本领域普通技术人员将能够没有困难地和在不付出创造性劳动的情况下从已知的主体材料中进行选择。
在本发明的一种另外的实施方案中,式(1)的化合物用作基质材料,与一种或多种掺杂剂、优选磷光掺杂剂组合。
在包含基质材料和掺杂剂的体系中的掺杂剂被认为是指在该混合物中比例较小的组分。相应地,在包含基质材料和掺杂剂的体系中的基质材料被认为是指在该混合物中比例较大的组分。
在此情况下所述基质材料在发光层中的比例按体积计在50.0%和 99.9%之间,优选按体积计在80.0%和99.5%之间,尤其优选地,对于荧光发光层,按体积计在92.0%和99.5%之间,而对于磷光发光层,按体积计在85.0%和97.0%之间。
相应地,所述掺杂剂的比例按体积计在0.1%和50.0%之间,优选按体积计在0.5和20.0%之间,尤其优选地,对于荧光发光层,按体积计在0.5%和8.0%之间,而对于磷光发光层,按体积在3.0%和15.0%之间。
有机电致发光器件的发光层也可包含含有多种基质材料(混合-基质体系)和/或多种掺杂剂的体系。在此情况下,所述掺杂剂同样通常是在该体系中比例较小的材料,而所述基质材料是在该体系中比例较大的材料。然而在个体情况下,在体系中的单独的基质材料的比例可小于单独的掺杂剂的比例。
在本发明的一种另外的优选实施方案中,式(1)化合物用作混合- 基质体系的组分。所述混合-基质体系优选包含两种或三种不同的基质材料,尤其优选两种不同的基质材料。在此处所述两种材料之一优选为具有空穴传输性质的材料,而另一种材料是具有电子传输性质的材料。但是,混合-基质组分的期望的电子传输和空穴传输性质也可主要地或完全地合并在单个混合-基质组分中,其中一种或多种另外的混合- 基质组分实现其它的功能。在此处两种不同的基质材料可以以1:50至 1:1的比例,优选1:20至1:1的比例,尤其优选1:10至1:1的比例和非常特别优选1:4至1:1的比例存在。混合-基质体系优选用于发磷光的有机电致发光器件中。特别是在申请WO 2010/108579中给出了混合-基质体系的更加确切的信息。
所述混合-基质体系可包含一种或多种掺杂剂,优选一种或多种磷光掺杂剂。通常,混合-基质系统优选用于发磷光的有机电致发光器件中。
取决于在混合-基质体系中使用什么类型的掺杂剂,可作为混合- 基质体系的基质组分与本发明化合物组合使用的尤其合适的基质材料,选自下文示出的用于磷光掺杂剂的优选基质材料或用于荧光掺杂剂的优选基质材料。
在混合-基质体系中使用的优选磷光掺杂剂是如在上文的表中所显示的磷光掺杂剂。
在本发明器件的相关功能中优选使用的材料在下文示出。
优选的荧光掺杂剂选自如下类的芳基胺。在本发明意义上的芳基胺或芳族胺被认为是指包含三个直接键合至氮的取代或未取代的芳族或杂芳族环系的化合物。这些芳族或杂芳族环系中的至少一个优选是稠合环系,特别优选具有至少14个芳族环原子。其优选的实例是芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族胺或芳族二胺。芳族蒽胺被认为是指其中一个二芳基氨基基团直接与蒽基团优选在9-位键合的化合物。芳族蒽二胺被认为是指其中两个二芳基氨基基团直接与蒽基团优选在9,10-位键合的化合物。以与此类似的方式,定义芳族的芘胺、芘二胺、胺和二胺,其中所述二芳基氨基基团优选与芘在1-位或在1,6-位键合。
除本发明的化合物外,优选用于荧光掺杂剂的合适的基质材料是来自多种类别的物质的材料。优选的基质材料选自如下的类:低聚亚芳基(例如,根据EP 676461的2,2',7,7'-四苯基螺二芴,或二萘基蒽),特别是含有稠合芳族基团的低聚亚芳基,低聚亚芳基亚乙烯基(例如根据EP 676461的DPVBi或螺-DPVBi),多足金属络合物(例如根据 WO 2004/081017的),空穴传导化合物(例如根据WO 2004/058911 的),电子传导化合物,特别是酮、氧化膦、亚砜等(例如根据WO 2005/084081和WO 2005/084082的),阻转异构体(例如根据WO2006/048268的),硼酸衍生物(例如根据WO 2006/117052的),或苯并蒽(例如根据WO 2008/145239的)。特别优选的基质材料选自如下的类别:含萘、蒽、苯并蒽和/或芘的低聚亚芳基或这些化合物的阻转异构体,低聚亚芳基亚乙烯基,酮,氧化膦和亚砜。非常特别优选的基质材料选自如下的类别:含蒽、苯并蒽、苯并菲和/或芘的低聚亚芳基或这些化合物的阻转异构体。在本发明意义上的低聚亚芳基旨在被认为是指其中至少三个芳基或亚芳基基团彼此键合的化合物。
除了本发明的化合物外,用于磷光掺杂剂的优选基质材料是芳族胺,特别是三芳基胺,例如根据US 2005/0069729的,咔唑衍生物(例如CBP, N,N-双咔唑基联苯)或根据WO2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851的化合物,桥连咔唑衍生物,例如根据WO 2011/088877和WO 2011/128017的,茚并咔唑衍生物,例如根据WO 2010/136109和WO 2011/000455的,氮杂咔唑衍生物,例如根据 EP 1617710、EP1617711、EP 1731584、JP 2005/347160的,吲哚并咔唑衍生物,例如根据WO 2007/063754或WO 2008/056746的,酮,例如根据 WO 2004/093207或WO 2010/006680的,氧化膦,亚砜和砜,例如根据 WO 2005/003253的,低聚亚苯基,双极性基质材料,例如根据WO 2007/137725的,硅烷,例如根据WO 2005/111172的,氮杂硼杂环戊二烯或硼酸酯,例如根据WO 2006/117052的,三嗪衍生物,例如根据WO 2010/015306、WO 2007/063754或WO 2008/056746的,锌络合物,例如根据EP 652273或WO 2009/062578的,铝络合物,例如BAlq,二氮杂硅杂环戊二烯和四氮杂硅杂环戊二烯衍生物,例如根据WO 2010/054729的,二氮杂磷杂环戊二烯衍生物,例如根据WO 2010/054730的,和铝络合物,例如BAlQ。
除了本发明的化合物外,可在本发明有机电致发光器件的空穴注入或空穴传输层中或电子传输层中使用的合适的电荷传输材料,例如是在Y. Shirota等人,Chem.Rev.(化学综述)2007,107(4),953-1010中公开的化合物,或根据现有技术用于这些层中的其它材料。
所述有机电致发光器件的阴极优选包含具有低逸出功的金属、金属合金或多层结构,其包含不同金属例如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)。同样合适的是包含碱金属或碱土金属和银的合金,例如包含镁和银的合金。在多层结构情况下,除所述金属之外,也可使用具有相对高逸出功的其它金属例如Ag 或Al,在这种情况下,通常使用金属的组合,例如Ca/Ag、Mg/Ag或Ba/Ag。也可以优选在金属阴极和有机半导体之间引入具有高介电常数的材料的薄中间层。适合于该目的的例如是碱金属氟化物或碱土金属氟化物,但也可以是相应的氧化物或碳酸盐(例如LiF、Li2O、BaF2、MgO、NaF、CsF、 Cs2CO3等)。此外,羟基喹啉锂(LiQ)可用于该目的。该层的层厚度优选为0.5至5nm。
所述阳极优选包含具有高逸出功的材料。所述阳极优选具有相对于真空大于4.5eV的逸出功。适于该目的的一方面是具有高氧化还原电势的金属,例如Ag、Pt或Au。另一方面,也可以优选金属/金属氧化物电极(例如Al/Ni/NiOx、Al/PtOx)。对于一些应用,至少一个电极必须是透明的或部分透明的,以利于有机材料辐射(有机太阳能电池),或耦合输出光 (OLED、O-LASER)。此处优选的阳极材料是导电的混合金属氧化物。特别优选氧化铟锡(ITO)或氧化铟锌(IZO)。此外优选导电的掺杂有机材料,特别是导电的掺杂聚合物。
所述器件被适当地(取决于应用)结构化,设置触点并且最终被密封,因为本发明器件的寿命在水和/或空气的存在下会缩短。
在一种优选的实施方案中,本发明有机电致发光器件的特征在于,通过升华工艺涂覆一个或多个层,其中在真空升华设备中,在小于10-5毫巴、优选小于10-6毫巴的初压下通过气相沉积施加所述材料。然而,所述初压在此处也可以甚至更低,例如小于10-7毫巴。
同样优选如下的有机电致发光器件,其特征在于,通过OVPD(有机气相沉积)方法或借助于载气升华来涂覆一个或多个层,其中,在 10-5毫巴至1巴的压力下施加所述材料。该方法中的特别的例子是OVJP (有机蒸气喷印)方法,其中所述材料通过喷管直接施加,并且因此是结构化的(例如M.S.Arnold等人,Appl.Phys.Lett.(应用物理快报) 2008,92,053301)。
此外还优选如下的有机电致发光器件,其特征在于从溶液中例如通过旋涂,或借助于任何希望的印刷方法例如丝网印刷、柔性版印刷、喷嘴印刷或平版印刷,但是特别优选LITI(光引发热成像,热转印) 或喷墨印刷,来产生一个或多个层。对于这种目的,可溶性的式(I)化合物是必要的。可通过适当取代所述化合物实来现足够的溶解性。
为制造本发明的有机电致发光器件,此外优选从溶液中施加一个或多个层和通过升华方法施加一个或多个层。
依照本发明,包含一种或多种式(I)化合物的电子器件可用于显示器中,用作在照明应用中的光源和用作在医学和/或美容应用(例如光线疗法)中的光源。
能够以非常通用的方式使用包含式(1)化合物的器件。因此,例如包含一种或多种式(I)化合物的电致发光器件可用于电视、移动电话、电脑和相机的显示器中。然而,所述器件也可用于照明应用中。另外,在例如OLED或OLEC中的包含至少一种式(I)化合物的电致发光器件,可用于医学或美容中的线疗法。因此,能够治疗大量的疾病(牛皮癣、异位性皮炎、炎症、痤疮、皮肤癌等)或者预防和减少皮肤皱纹、皮肤发红和皮肤老化。另外,可使用所述发光器件以保持饮料、饭菜或食物新鲜或使设备(例如医学设备)无菌。
本发明因此还涉及包含至少一种本发明化合物的电子器件、优选有机电致发光器件、非常优选OLED或OLEC,其用于在医学中的光治疗用途,优选用于治疗皮肤疾病,非常优选用于治疗牛皮癣、异位性皮炎、神经性皮炎、皮肤癌、皮肤炎症、黄疸(黄疸病)和新生儿黄疸。
本发明还涉及包含至少一种本发明化合物的电子器件、优选有机电致发光器件、非常优选OLED或OLEC在美容中的用途,其优选用于治疗痤疮、皮肤发红,用于治疗皮肤老化(抗老化),用于减少皮肤皱纹和用于治疗脂肪团。
本发明的化合物和本发明的有机电致发光器件相对于现有技术的突出之处在于如下令人预料不到的优势:
1.本发明的化合物非常适合用于电子器件的空穴传输层或空穴注入层中,例如用于有机电致发光器件中,这特别是由于它们具有高的空穴迁移率。
2.本发明的化合物具有相对低的升华温度、高的温度稳定性和高的氧化稳定性和高的玻璃转化温度,这对于例如从溶液中或从气相中的可加工性和对于在电子器件中的用途都是有利的。
3.本发明化合物在电子器件中的使用,特别是用作空穴传输或空穴注入材料,以及用作发光材料,产生高效率、低的工作电压和产生长寿命。
应当指出,在本发明描述的实施方案的变体落在本发明的范围内。除非明确地排除,否则在本发明公开的每一特征,可由用于相同、等同或相似目的的可选特征代替。因此,除非另有说明,否则本发明公开的每一特征被视为上位系列的实例或被视为等同或相似的特征。
本发明的所有特征能够以任何方式互相组合,除非特定的特征和/ 或步骤是互斥的。这特别地适用于本发明的优选特征。同样地,非必要性组合的特征可单独地(和非组合方式地)使用。
还应指出,许多特征,尤其是本发明优选实施方案的那些特征,本身是创造性的并且不应仅仅被视为本发明实施方案的一部分。对于这些特征,可另外地或者作为目前要求保护的每一发明的可选方案,寻求单独的保护。
可对本发明公开的技术作用的教导进行提取,并且可与其它实施例相结合。
具体实施方案
通过如下的实施例更详细地解释本发明,但不希望因此限制本发明。
实施例
材料
材料HIL1、HIL2(EP 0676461)、H1(WO 2008/145239)、ETM1(WO 2005/053055)、SEB1(WO 2008/006449)、LiQ和NPB对于本领域普通技术人员是公知的。从现有技术已知它们的性质和合成。化合物(1-9)、 (1-1)、(1-11)、(1-12)、(2-6)(1-2)和(4-1)是根据本发明的化合物。
实施例1
联苯-4-基-(9,9-二甲基-9H-芴-2-基)菲-3-基胺(1-1)的合成
原料3-溴菲的合成
3-氨基菲的合成
将50g(227mmol)3-乙酰基菲和63.8ml(790mmol)吡啶和 42g(592mmol)羟基氯化铵溶于300mL的EtOH中。将该批料加热至75 ℃。反应1小时后将该批料冷却。然后将该混合物分配在乙酸乙酯和水之间,将有机相用水洗涤三次并且用Na2SO4干燥并且在旋转蒸发仪中浓缩。将300ml多磷酸小心地加入浓缩的溶液中,并且将混合物在 75℃下加热1小时。然后将该批料冷却至室温,并且小心地倒入冰水 (300ml)。用抽滤过滤析出的固体并用甲醇冲洗。最后,将800ml MeOH 和70ml浓HCl添加至该固体。将反应混合物在沸腾下加热8小时。然后用氢氧化钠溶液中和混合物,在乙酸乙酯和水之间分配,将有机相用水洗涤三次并且用Na2SO4干燥,并且在旋转蒸发仪中蒸发。将残留物在40℃真空干燥。产率:35.5g(184mmol)(理论值的81%)。
3-溴菲的合成
将30g(155mmol)3-氨基菲和36.7g(155mmol)CuBr2溶于300ml的干燥乙腈中。将40.4ml亚硝酸叔丁酯(535mmol)在0℃下分份添加。将该悬浮液再搅拌1小时,然后倒入400ml冰水中并且搅拌约20分钟。将析出的固体用抽滤过滤,溶于二氯甲烷并且用水洗涤多次。将有机相在旋转蒸发仪中蒸发,并且从甲苯/庚烷中重结晶。产率: 21.9g(85mmol)(理论值的55%)。
可类似地制备作为起始化合物其它卤化菲。
化合物(1-1)的合成
将28.1g(78mmol)联苯-4-基-(9,9-二甲基-9H-芴-2-基)胺、 20.0g(78mol)3-溴菲溶于600ml甲苯中:将溶液脱气并且用N2饱和。然后加入3.1ml(3.11mmol)三叔丁基磷溶液和0.35g(1.56mmol)醋酸钯(II),并且其后加入11.6g叔丁醇钠(116.7mmol)。将反应混合物在保护性气氛下在沸腾下加热5小时。其后将混合物分配在甲苯和水之间,将有机相用水洗涤三次并且用Na2SO4干燥,并且在旋转蒸发仪中蒸发。在用甲苯将粗产物经过硅胶过滤以后,将剩下的残余物从庚烷/甲苯中重结晶,并且最终在高真空下升华,纯度是99.9%(HPLC)。化合物(1-1)的产率是 29.6g(理论值的71%)。
实施例2–12
化合物(1-2)至(1-12)的合成
与实施例1中描述的化合物(1-1)的合成类似,还制备如下的化合物(1-2)至(1-12)。
与在实施例1中描述的化合物(1-1)的合成类似,还制备如下的对比化合物(HTMV1)至(HTMV3)和(HTMV6)至(HTMV7)。
实施例13
化合物N*4'*-联苯-4-基-N*4'*-二苯并呋喃-4-基-N*4*-菲-3-基 -N*4*-苯基联苯-4,4'-二胺(2-1)的合成
将10g菲-3-基苯基胺(37mmol)、21g联苯-4-基-(4'-溴联苯-4-基)二苯并呋喃-4-基胺(37mol)溶于500ml甲苯中:将溶液脱气并用N2饱和。然后加入1.5ml(1.5mmol)三叔丁基膦溶液和0.17g(0.74mmol)醋酸钯 (II),并且其后加入5.6g叔丁醇钠(56mmol)。将反应混合物在保护性气氛下在沸腾下加热3小时。其后将混合物分配在甲苯和水之间,将有机相用水洗涤三次并且用Na2SO4干燥,并且在旋转蒸发仪中蒸发。在用甲苯将粗产物经过硅胶过滤以后,使剩下的残余物从庚烷/甲苯中重结晶,并且最终在高真空下升华,纯度是99.9%(HPLC)。产率是16.8g(理论值的60%)。
实施例14–18
化合物(2-2)至(2-6)的合成
与在实施例13中描述的化合物(2-1)的合成类似,还制备如下的化合物(2-2)至(2-6)。
与在实施例13中描述的化合物(2-1)的合成类似,还制备对比化合物(HTMV5)。
实施例19
化合物联苯-4-基联苯-2-基-(9,9-二甲基-7-菲-3-基-9H-芴-2-基)胺 (3-1)的合成
3-(7-溴-9,9-二甲基-9H-芴-2-基)菲
将52g(164mmol)7-溴(9,9-二甲基芴-2-基)硼酸(CAS号: 1213768-48-9)、50g(164mmol)3-碘菲和205ml的2M NaHCO3水溶液 (327mmol)悬浮在800ml二甲氧基乙烷中。将3.8g(3.3mmol)四(三苯基) 膦钯(0)加入到该悬浮液中,并且将反应混合物回流加热16小时。在冷却后,将有机相分离、经过硅胶过滤、用300mL水洗涤3次并且其后蒸发至干。用庚烷/乙酸乙酯(20:1)将粗产物经过硅胶过滤,得到 55g(75%)的3-(7-溴-9,9-二甲基-9H-芴-2-基)菲。
联苯-4-基联苯-2-基-(9,9-二甲基-7-菲-3-基-9H-芴-2-基)胺
将19.2g联苯-4-联苯-2-基胺(60mmol)、26.9g 3-(7-溴-9,9-二甲基-9H-芴-2-基)菲(60mol)溶于500ml甲苯中:将溶液脱气并且用N2饱和。加入3.2g(3.9mmol)三叔丁基膦溶液和0.27g(1.2mmol)醋酸钯(II),并且其后加入8.9g叔丁醇钠(56mmol)。将反应混合物在保护性气氛下在沸腾下加热4小时。其后将混合物分配在甲苯和水之间,将有机相用水洗涤三次并且用Na2SO4干燥,并且在旋转蒸发仪中蒸发。在用甲苯将粗产物经过硅胶过滤以后,使剩下的残留物从庚烷/甲苯中重结晶,并且最终在高真空下升华,纯度是99.9%。产率是28g(理论值的68%)。
实施例20–22
化合物(3-2)至(3-4)的合成
与在实施例18中描述的合成类似,制备起始化合物。
与在实施例19中描述的化合物(3-1)的合成类似,制备化合物(3-2) 至(3-4)。
与在实施例19中描述的化合物(3-1)的合成类似,还制备对比化合物(V4)。
实施例23-25
化合物(9,9-二甲基-9H-芴-2-基)-(9,9-二苯基-9H-芴-4-基)菲-3-基胺(4-1)、(4-2和(4-3)的合成
(9,9-二甲基-9H-芴-2-基)菲-3-基胺
将18.4g(95.29mmol)3-氨基菲、26g(95.4mmol)2-溴芴和 18.3g(190mmol)叔丁醇钠悬浮在350ml甲苯中。向该悬浮液中加入 1.07g(4.76mmol)醋酸钯和2.64g 1,1-双(二苯基膦)二茂铁(4.76mmol)。将反应混合物回流加热16小时。冷却后,将有机相分离并用200mL水洗涤三次,并且其后蒸发至干。使残留物从甲苯中重结晶(31g,85%产率)。
(9,9-二甲基-9H-芴-2-基)-(9,9-二苯基-9H-芴-4-基)菲-3-基胺(4-1)
将13.1g(9,9-二甲基-9H-芴-2-基)菲-3-基胺(34mmol),13.5g 4-溴 -9,9-二苯基-9H-芴(34mol)溶于300mL甲苯中:将溶液脱气并用N2饱和。然后加入1.4ml(0.68mmol)1M三叔丁基膦溶液和0.153g(0.68mmol)醋酸钯(II),并且其后加入6.5g叔丁醇钠(68mmol)。将反应混合物在保护性气氛下在沸腾下加热4小时。其后将混合物分配在甲苯和水之间,将有机相用水洗涤三次并且用Na2SO4干燥,并且在旋转蒸发仪中蒸发。在用甲苯将粗产物经过硅胶过滤以后,使剩下的残余物从庚烷/甲苯中重结晶,并且最终在高真空下升华,纯度是99.9%。产率是14.3g(理论值的60%)。
类似地制备如下的化合物:
实施例26
化合物的表征
通过依照WO 2004/058911的一般方法制备本发明OLED和依照现有技术的OLED,此处将该方法调整以适应所述环境(层厚度变化、材料等)。
在以下实施例中示出多种OLED的数据(见表1和表2)。使用的基底是如下的玻璃板,其涂有50nm厚度的结构化ITO(氧化铟锡)。所述OLED 原则上具有如下的层结构:基底/空穴注入层(HIL1)/空穴传输层(HIL2)/ 空穴注入层(HIL3)/电子阻挡层(EBL)/发光层(EML)/电子传输层(ETL)/ 电子注入层(EIL)和最终的阴极。通过厚度100nm的铝层形成阴极。所述OLED的确切结构显示于表1中。制造OLED所需的材料在上文中示出。
在真空室中通过热气相沉积施加所有材料。此处的发光层总是由至少一种基质材料(主体材料)和发光掺杂剂(发光体)组成,通过共蒸发使所述一种或多种基质材料以特定的体积比例与所述发光掺杂剂混合。此处例如H1:SEB1(95%:5%)的表达是指,材料H1以95%的体积比例存在于该层中,而SEB1以5%的比例存在于该层中。类似地,所述电子传输层也可由两种材料的混合物组成。
通过标准的方法表征所述OLED。为此目的,确定电致发光光谱、电流效率(以cd/A测量)、从呈现朗伯发射特性的电流/电压/发光密度特性线(IUL特性线)计算的作为发光密度函数的功率效率(以lm/W 测量)和外量子效率(EQE,以百分比测量),以及寿命。确定在1000cd/m2发光密度下的电致发光光谱,并从其计算CIE 1931x和y颜色坐标。术语在1000cd/m2下的EQE表示在1000cd/m2的工作发光密度下的外量子效率。在6000cd/m2下的LT80是所述OLED从6000cd/m2的亮度下降至起始强度的80%即下降至4800cd/m2所经历的寿命。多种OLED的数据被总结在表2中。
将本发明化合物作为基质材料用于发荧光OLED中
本发明化合物尤其适合作为在OLED中的HIL、HTL或EBL。它们适合作为单层,但也适合作为用作HIL、HTL、EBL或在EML中的混合组分。
与NPB参照化合物(V1)相比,包含本发明化合物的所有样品都显示出更高的效率和在单一蓝色方面显著改进的寿命。
与参照材料HTMV1-HTMV5(V2-V6)相比,本发明化合物(1-9)、 (1-1)和(1-11)具有更好的效率和改进的寿命。与HTMV6和HTMV7(V7 和V8)相比,本发明的化合物(1-1)具有显著改进的寿命。
与对比例V1至V8相比,实施例E0展现了显著改进的LT50值。另外,与对比例相比以及与E0相比,都可通过所述菲实现显著的改进,所述菲除了3位外没有另外的芳族和/或杂芳族取代(E1至E7)。化合物 (2-6)(E5)可与NPB(V1)直接比较。可以看出,化合物(2-6)导致器件具有显著改进的EQE值,特别是导致改进的LT80值。
Claims (11)
1.通式(4a)的化合物
其中如下适用于出现的符号和标记:
L是单键或具有12至40个环原子的二价的芳基或杂芳基基团,所述芳基或杂芳基基团可被一个或多个基团R2取代,其中,如果L是单键,则氮直接键合至所述菲的3位,其中L优选是单键;
Ar1选自式(8)至(106)的基团,Ar2选自式(9)至(106)的基团:
R1是H;
R4在每次出现时相同或不同地是H,D,F,Cl,Br,I,C(=O)R2,CN,Si(R2)3,NR2,NO2,P(=O)(R2)2,S(=O)R2,S(=O)2R2,具有1至20个C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至20个C原子的支链或环状烷基、烷氧基或硫代烷基基团或者具有2至20个C原子的烯基或炔基基团,其中上面提到的基团中的每个可被一个或多个基团R2取代,和其中在上面提到的基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有6至30个芳族环原子的芳族环系,所述芳族环系可在每种情况下被一个或多个基团R2取代,其中两个或更多个基团R4可互相地连接和可形成环;
R2在每次出现时相同或不同地是H,D,F,Cl,Br,I,C(=O)R3,CN,Si(R3)3,NO2,P(=O)(R3)2,S(=O)R3,S(=O)2R3,具有1至20个C原子的直链烷基、烷氧基或硫代烷基基团或者具有3至20个C原子的支链或环状烷基、烷氧基或硫代烷基基团或者具有2至20个C原子的烯基或炔基基团,其中上面提到的基团中的每个可被一个或多个基团R3取代,和其中在上面提到的基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至30个芳族环原子的芳族或杂芳族环系,其可在每种情况下被一个或多个基团R3取代,或具有5至30个芳族环原子的芳氧基或杂芳氧基基团,其可被一个或多个基团R3取代,其中两个或更多个基团R2可互相地连接和可形成环;
R3在每次出现时相同或不同地是H,D,F,或具有1至20个C原子的脂族的、芳族的或杂芳族的有机基团,其中一个或多个H原子还可被D或F代替;两个或更多个取代基R3在此处可互相地连接和可形成环;
其中除了所述菲以及由Ar1和Ar2限定的其它基团以外,式(4a)的化合物不包含另外的具有多于10个环原子的稠合的芳族或杂芳族环。
2.根据权利要求1所述的化合物,其特征在于所述化合物包含总共至少26个环原子。
3.根据权利要求1或2所述的化合物,其特征在于所述化合物只含有一个胺基团。
4.一种用于制备根据权利要求1至3中的任一项所述的化合物的方法,所述方法通过含有离去基团的菲衍生物与Ar2-NH-Ar1反应的一步Buchwald偶联进行制备。
5.一种用于制备根据权利要求1至3中的任一项所述的化合物的方法,所述方法通过含有离去基团的菲衍生物与(1)Ar2-NH2和(2)NH2-Ar1的逐步反应的两步Buchwald偶联进行制备。
6.含有一种或多种根据权利要求1至3中的任一项所述的化合物的低聚物、聚合物或树枝状大分子,其中形成所述聚合物、低聚物或树枝状大分子的键可位于在式(4a)中由R4、R2或菲基团上的H取代的任何期望的位置处。
7.一种包含一种或多种根据权利要求1至3中的任一项所述的化合物和至少一种另外的有机功能材料的组合物,所述有机功能材料选自荧光发光体、磷光发光体、主体材料、基质材料、电子传输材料、电子注入材料、空穴导体材料、空穴注入材料、电子阻挡材料和空穴阻挡材料。
8.一种制剂,其包含至少一种根据权利要求1至3中的任一项所述的化合物或至少一种根据权利要求6所述的聚合物、低聚物或树枝状大分子或至少一种根据权利要求7所述的组合物和至少一种溶剂。
9.一种电子器件,其包含至少一种根据权利要求1至3中的任一项所述的化合物或至少一种根据权利要求6所述的聚合物、低聚物或树枝状大分子或至少一种根据权利要求7所述的组合物。
10.根据权利要求9所述的电子器件,其特征在于所述电子器件选自有机集成电路(O-IC)、有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机太阳能电池(O-SC)、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)和有机电致发光器件(OLED)。
11.根据权利要求9所述的电子器件,其中所述电子器件选自有机发光二极管(OLED)。
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JP6553241B2 (ja) | 2019-07-31 |
US20190393414A1 (en) | 2019-12-26 |
KR102095704B1 (ko) | 2020-04-01 |
CN104364245B (zh) | 2017-10-03 |
US20150155491A1 (en) | 2015-06-04 |
KR102238204B1 (ko) | 2021-04-08 |
US10446759B2 (en) | 2019-10-15 |
KR20220139455A (ko) | 2022-10-14 |
WO2013182263A1 (de) | 2013-12-12 |
CN104364245A (zh) | 2015-02-18 |
EP2858980A1 (de) | 2015-04-15 |
US9799833B2 (en) | 2017-10-24 |
KR20200035475A (ko) | 2020-04-03 |
US11424411B2 (en) | 2022-08-23 |
DE102012011335A1 (de) | 2013-12-12 |
KR102452746B1 (ko) | 2022-10-07 |
KR20210041112A (ko) | 2021-04-14 |
KR20170106481A (ko) | 2017-09-20 |
EP2858980B1 (de) | 2019-06-26 |
JP2018150306A (ja) | 2018-09-27 |
CN107721861B (zh) | 2021-04-16 |
JP2015529632A (ja) | 2015-10-08 |
US20180102479A1 (en) | 2018-04-12 |
KR20150023657A (ko) | 2015-03-05 |
JP6324950B2 (ja) | 2018-05-16 |
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