CN105593213B - 作为用于电子器件的材料的三芳基胺取代的苯并[h]喹啉-衍生物 - Google Patents
作为用于电子器件的材料的三芳基胺取代的苯并[h]喹啉-衍生物 Download PDFInfo
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- CN105593213B CN105593213B CN201480054649.XA CN201480054649A CN105593213B CN 105593213 B CN105593213 B CN 105593213B CN 201480054649 A CN201480054649 A CN 201480054649A CN 105593213 B CN105593213 B CN 105593213B
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- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZSVHUITUMSDFCK-UHFFFAOYSA-N isoquinoline;quinoline Chemical compound C1=NC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 ZSVHUITUMSDFCK-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
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- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
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- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 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
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
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- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005054 naphthyridines Chemical class 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
- CDKDZKXSXLNROY-UHFFFAOYSA-N octylbenzene Chemical compound CCCCCCCCC1=CC=CC=C1 CDKDZKXSXLNROY-UHFFFAOYSA-N 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
- 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
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 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
- 238000007789 sealing 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
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 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
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Abstract
本发明涉及根据式(I)的杂芳基化合物,并涉及其在电子器件中的用途。
Description
本申请涉及下文定义的根据式(I)的菲咯啉的杂芳族类似物。该化合物适合于作为电子器件特别是有机电致发光器件(OLED)中的功能材料等。
理解在本申请的上下文中的电子器件表示被称为有机电子器件的事物,所述有机电子器件含有有机化合物作为功能材料。更具体地,理解这些表示OLED。
其中使用有机化合物作为功能材料的OLED的结构描述在例如US 4539507、US5151629、EP 0676461和WO 98/27136中。通常,理解术语OLED表示具有一个以上包含有机化合物并在施加电压时发光的层的电子器件。
在电子器件特别是OLED中,对于改进性能数据特别是寿命、效率和工作电压有着巨大的兴趣。在这些方面,还不可能找到任何完全令人满意的方案。
具有空穴传输功能的层,例如空穴注入层、空穴传输层、电子阻挡体层和发射层,对电子器件的性能数据有巨大的影响。为了在这些层中的用途,在继续寻找新型的具有空穴传输性质的材料,例如空穴注入材料、空穴传输材料、电子阻挡体材料和基体材料,用于与发射体材料特别是磷光发射体材料组合使用。
为此目的,现有技术描述了单三芳基胺(参见JP 1995/053955、WO 2006/123667和JP 2010/222268)和双官能化或多官能度胺(参见US 7504163和US 2005/0184657)等。此外,对于此目的来说已知的是咔唑化合物,例如双咔唑联苯(CBP),和在WO 2008/086851、US2005/0221124 A1、EP 2202818 A1和WO 2013/060418中描述的化合物。此外,对于此目的来说已知的是桥联的三芳基胺化合物,如例如在WO 2007/031165、WO 2010/083871、WO 2011/088877、WO 2011/107186和WO 2011/128017中所述的。
然而,对于用于此用途的备选化合物存在不变的需要。
现在已经发现,其特征在于它们具有苯并[h]喹啉单元的芳基胺、桥联的芳基胺和咔唑衍生物突出地适合于用在OLED中。
这些化合物优选具有选自非常好的空穴传导性和高的热和氧化稳定性中的一个或多个有利的性质。更具体地,化合物具有与类似结构的其他化合物相比比较高能量的HOMO,并且因此是出色的空穴传导体。在用于OLED的情况下,化合物优选达到高寿命和低工作电压。
本申请因此提供了式(I)的化合物
式(I)
其中:
A选自式(A-1)和(A-2)的基团
式(A-1)
式(A-2),
其经由用*标记的键结合,
Ar1在各个情况下是相同或不同的,并且是芳族或杂芳族环体系,所述体系具有5至24个芳族环原子并且可以被一个以上R1基团取代;
Ar2在各个情况下是相同或不同的,并且是芳族或杂芳族环体系,所述体系具有5至24个芳族环原子并且可以被一个以上R1基团取代;
X在各个情况下是相同或不同的,并且是单键或选自BR2、C(R2)2、-C(R2)2-C(R2)2-、-C(R2)=C(R2)-、-C(R2)2-O-、-C(R2)2-NR2-、Si(R2)2、C=O、NR2、PR2、P(=O)R2、O、S、S=O和SO2的基团;
R1、R2在各个情况下是相同或不同的,并且是H、D、F、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3,具有1至20个碳原子的直链烷基或烷氧基或者具有3至20个碳原子的支链的或环状的烷基或烷氧基或者具有2至20个碳原子的烯基或炔基,其中上述基团可以各自被一个以上R3基团取代并且其中在上述基团中的一个以上CH2基团可以被-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2替换,或具有5至30个芳族环原子并可以被一个以上R3基团取代的芳族或杂芳族环体系;两个以上R1或R2基团可以相互接合并形成环;
R3在各个情况下是相同或不同的,并且是H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4,具有1至20个碳原子的直链烷基或烷氧基或者具有3至20个碳原子的支链的或环状的烷基或烷氧基或者具有2至20个碳原子的烯基或炔基,其中上述基团可以各自被一个以上R4基团取代并且其中在上述基团中的一个以上CH2基团可以被-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-O-、-S-、SO或SOO替换,或具有5至30个芳族环原子并可以被一个以上R4基团取代的芳族或杂芳族环体系;两个以上R3基团可以相互接合并形成环;
R4在各个情况下是相同或不同的,并且是H、D、F、CN或具有1至20个碳原子的脂族、芳族或杂芳族有机基团,其中一个以上氢原子也可以被D、F或CN替换;两个以上R4取代基可以相互接合并形成环;
n是0、1、2或3;
i在各个情况下是相同或不同的,并且是0或1;并且
在中央画有N的苯环中,一个以上环成员-CR1=在各情况下可以被-N=替换。
在本发明的上下文中的芳基含有6至60个芳族环原子;在本发明的上下文中的杂芳基含有5至60个芳族环原子,其中至少一个是杂原子。杂原子优选选自N、O和S。这是基本的定义。如果在本发明的说明书中陈述了其他优选,例如关于芳族环原子的数量或存在的杂原子的数量,使用这些。
在此理解芳基或杂芳基表示简单的芳族环,即苯,或简单的杂芳族环,例如吡啶、嘧啶或噻吩,或稠合的(由环组成的)芳族或杂芳族多环,例如萘、菲、喹啉或咔唑。在本申请的上下文中,稠合的(由环组成的)芳族或杂芳族多环由两个以上相互稠合的简单芳族或杂芳族环组成。
特别地理解其中每个可以被上述基团取代并且可以经由任何想要的位置接合在芳族体系或杂芳族体系上的芳基或杂芳基表示源自苯、萘、蒽、菲、芘、二氢芘、苝、三亚苯、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、噻吩、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、吲嗪和苯并噻二唑的基团。
在本发明的上下文中,芳族环体系在环体系中含有6至60个碳原子。在本发明的上下文中,杂芳族环体系含有5至60个芳族环原子,其中至少一个是杂原子。杂原子优选选自N、O和/或S。在本发明的上下文中,应当理解芳族或杂芳族环体系表示一种体系,其不必须仅含有芳基或杂芳基,而是其中对于多个芳基或杂芳基来说也可以通过单键或通过非芳族单元(例如一个以上任选取代的C、Si、N、O或S原子)键合。在这种情况下,基于体系中除H之外的原子的总数,所述非芳族单元包含优选少于10%的除H之外的原子。例如,在本发明的上下文中,如9,9’-螺环双芴、9,9’-二芳基芴、三芳基胺、二芳基醚和茋的体系也被认为是芳族环体系,并且其中两个以上芳基例如通过直链或环状烷基、烯基或炔基或通过硅烷基接合的体系也是一样。此外,在本发明的上下文中,其中两个以上芳基或杂芳基经由单键相互接合的体系也被认为是芳族或杂芳族环体系,例如如联苯、三联苯或二苯基三嗪的体系。
特别地理解还可以在各情况下被上文定义的基团取代的、并且可以经由想要的位置接合在芳族体系或杂芳族体系上的具有5-60个芳族环原子芳族或杂芳族环体系表示源自上述在芳基和杂芳基范围内的基团和也源自联苯、三联苯、四联苯、芴、螺环双芴、二氢菲、二氢芘、四氢芘、茚并芴、三聚茚(truxene)、异三聚茚、螺环三聚茚、螺环异三聚茚、茚并咔唑或它们的组合的基团。
在本发明的上下文中,优选理解其中单独的氢原子或CH2也可以被上文在基团的定义中提及的基团取代的具有1至40个碳原子的直链烷基和具有3至40个碳原子的支链或环状烷基和具有2至40个碳原子的烯基或炔基表示甲基、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。优选理解具有1至40个碳原子的烷氧基或硫代烷基表示甲氧基、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、甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基、正戊基硫基、仲戊基硫基、正己基硫基、环己基硫基、正庚基硫基、环庚基硫基、正辛基硫基、环辛基硫基、2-乙基己基硫基、三氟甲基硫基、五氟乙基硫基、2,2,2-三氟乙基硫基、乙烯基硫基、丙烯基硫基、丁烯基硫基、戊烯基硫基、环戊烯基硫基、己烯基硫基、环己烯基硫基、庚烯基硫基、环庚烯基硫基、辛烯基硫基、环辛烯基硫基、乙炔基硫基、丙炔基硫基、丁炔基硫基、戊炔基硫基、己炔基硫基、庚炔基硫基或辛炔基硫基。
在本申请的上下文中,两个以上基团一起可以形成环的措辞应当理解为表示两个基团通过化学键相互接合等。然而,此外,上述措辞应当也理解为表示如果两个基团中的一个是氢,第二基团结合至氢原子键合的位置而形成环。
优选地,式(I)的化合物除了A基团之外不包含任何另外的芳基氨基、任何另外的桥联的芳基氨基或任何另外的咔唑基。理解桥联的芳基氨基表示对应于式(A-1)或(A-2)的其中存在至少一个不是单键的X桥的基团的基团。
此外,优选的是,式(I)的化合物不具有任何具有大于14个芳族环原子的稠合芳基或杂芳基(更优选任何具有大于10个芳族环原子的稠合芳基或杂芳基)作为取代基R1、R2、R3和R4。
对于式(I)的化合物来说,优选的是,在中央画有N的苯环中,没有环成员-CR1=被-N=替换,或者精确地,一个或两个环成员-CR1=被-N=替换,更优选没有环成员-CR1=被-N=替换,或者优选地,一个环成员-CR1=被-N=替换,且最优选没有环成员-CR1=被-N=替换。
在本发明的一个优选的实施方案中,在式(I)中的三个苯环中的中间一个中的正好一个或正好两个环成员-CR1=被-N=替换,且在两个外侧环中没有环成员-CR1=被-N=替换。
在本发明的备选的优选的实施方案中,在式(I)的全部三个在中央画有N的苯环中,没有环成员-CR1=被N替换。
优选的是,n是0、1或2,更优选0或1,最优选0。
优选的是,Ar1在各个情况下是相同或不同的,并且是芳族或杂芳族环体系,所述体系具有6至14芳族环原子并且可以被一个以上R1基团取代。更优选地,Ar1在各个情况下是相同或不同的,并且选自苯、吡啶、嘧啶、三嗪、萘、喹啉、芴、螺环双芴、茚并芴、咔唑、茚并咔唑、吲哚并咔唑、二苯并呋喃和二苯并噻吩,它们中的每个可以被一个以上R1基团取代。
最优选地,-(Ar1)n-单元在各个情况下是相同或不同的,并且选自下式(L-1)至(L-18)的基团:
其中所述基团各自可以被R1基团在未占据的位置取代,并且其中虚线表示到化合物的剩余部分的键。
R1优选在各个情况下是相同或不同的,并且是H、D、F、CN、Si(R3)3、N(R3)2,具有1至20个碳原子的直链烷基或烷氧基或者具有3至20个碳原子的支链的或环状的烷基或烷氧基,其中上述基团可以各自被一个以上R3基团取代并且其中在上述基团中的一个以上CH2基团可以被-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-替换,或具有5至20个芳族环原子的芳族或杂芳族环体系,其各自可以被一个以上R3基团取代,其中两个以上R1基团可以相互接合并可以形成环。
R2优选在各个情况下是相同或不同的,并且是H、D、F、Si(R3)3,具有1至20个碳原子的直链烷基或烷氧基或者具有3至20个碳原子的支链的或环状的烷基或烷氧基,其中上述基团可以各自被一个以上R3基团取代并且其中在上述基团中的一个以上CH2基团可以被-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-替换,或具有5至20个芳族环原子的芳族或杂芳族环体系,其各自可以被一个以上R3基团取代,其中两个以上R2基团可以相互接合并可以形成环。
在一个优选的实施方案中,两个结合至X基团的同一原子的、例如结合至是C(R2)2的X基团的碳原子的R2基团一起形成环。更优选地,在这种情况下,它们形成环烷基环,例如环戊基环或环己基环。
R3优选在各个情况下是相同或不同的,并且是H、D、F、CN、Si(R4)3、N(R4)2,具有1至20个碳原子的直链烷基或烷氧基或者具有3至20个碳原子的支链的或环状的烷基或烷氧基,其中上述基团可以各自被一个以上R4基团取代并且其中在上述基团中的一个以上CH2基团可以被-C≡C-、-R4C=CR4-、Si(R4)2、C=O、C=NR4、-NR4-、-O-、-S-、-C(=O)O-或-C(=O)NR4-替换,或具有5至20个芳族环原子的芳族或杂芳族环体系,其各自可以被一个以上R4基团取代,其中两个以上R3基团可以相互接合并可以形成环。
对于式(A-2)的基团来说,优选的是,没有指数i是1,精确地,一个或两个指数i是1,且其他指数i是0。
此外,优选的是,在式(A-2)的一个基团中存在不多于两个是单键的X基团。
优选的是X在各个情况下是相同或不同的,并且从单键或选自C(R2)2、-C(R2)2-C(R2)2-、-C(R2)=C(R2)-、C=O、NR2、O和S的基团中选出。最优选地,X在各个情况下是相同或不同的,并且从单键或选自C(R2)2、C=O、NR2、O和S的基团中选出。
优选的是,Ar2在各个情况下是相同或不同的,并且是芳族或杂芳族环体系,所述体系具有6至24芳族环原子并且可以被一个以上R1基团取代。更优选地,Ar2在各个情况下是相同或不同的,并且选自苯、联苯、三联苯、四联苯、吡啶、嘧啶、吡嗪、哒嗪、三嗪、萘、喹啉、芴、螺环双芴、茚并芴、咔唑、茚并咔唑、吲哚并咔唑、二苯并呋喃和二苯并噻吩,其中每个可以被一个以上R1基团取代。最优选地,Ar2在各个情况下是相同或不同的,并且选自苯、联苯、三联苯、四联苯、芴、螺环双芴、茚并芴、咔唑、茚并咔唑、吲哚并咔唑、二苯并呋喃和二苯并噻吩,其中每个可以被一个以上R1基团取代。
式(A-1)的基团的优选的实施方案是下式(A-1-1)至(A-1-30):
其可以各自被R1基团在未占据的位置取代。对于式(A-1-1),优选的是,Ar2在各个情况下是相同或不同的,并且选自苯、联苯、三联苯、四联苯、芴、螺环双芴、茚并芴、咔唑、茚并咔唑、吲哚并咔唑、二苯并呋喃和二苯并噻吩,其中每个可以被一个以上R1基团取代。
式(A-2)的基团的优选的实施方案是下式(A-2-1)至(A-2-59):
其可以各自被R1基团在未占据的位置取代。对于Ar2,优选的是,它在各个情况下是相同或不同的,并且选自苯、联苯、三联苯、四联苯、芴、螺环双芴、茚并芴、咔唑、茚并咔唑、吲哚并咔唑、二苯并呋喃和二苯并噻吩,其中每个可以被一个以上R1基团取代。
优选的式(I)的化合物对应于式(I-1)至(I-3)中的一个。
其中出现的基团和指数如上文所定义。同时,上文详述的基团和指数优选的实施方案是优选的。
更具体地,优选的是,对于式(I-1)至(I-3)来说,A基团选自式(A-1)和(A-2)的基团的优选的实施方案,尤其是选自式(I-1-1)至(I-1-30)和(I-2-1)至(I-2-59)的基团。
再一次地,尤其优选的是,对于式(I-1)至(I-3)来说,-[Ar1]n-单元选自上文列出的式(L-1)至(L-18)。
再一次地,尤其优选的是,对于式(I-1)至(I-3)来说,n是0。
在式(I-1)至(I-3)中,式(I-1)是特别优选的。
式(I)的化合物的实例列在下面。
本发明的化合物的合成可以通过现有技术中已知的方法或反应类型进行,如卤化、Buchwald偶联和Suzuki偶联。
方案1显示了用于制备本发明的化合物的优选合成路径。为了本发明的化合物的合成,使苯并[h]喹啉化合物A与式Ar-NH-Ar的胺B以Buchwald偶联反应。在此方案和在随后的方案中,化合物以未取代的形式示出。它们可以备选地提供有任何想要的取代基。
方案1
Y=离去基团,例如卤素
Ar=芳族或杂芳族环体系
n=0,1,2或3
中央有N的苯环:一个或多个环原子可以被N替换
对于本发明的化合物的制备来说另一个优选的合成路径示于方案2中。该合成路径包括两个偶联反应:首先,使苯并[h]喹啉化合物A与式Ar-NH2的胺C以第一Buchwald偶联反应。最后,用化合物D例如用溴芳基化合物完成第二Buchwald偶联。
方案2
可变基团的定义:见上文
k=0-10
用于本发明的化合物的合成中的初始化合物A的合成路径对于本领域技术人员来说是公知的。此外,在工作例中,详细说明一些清楚的合成方法。
另一个合适的用于制备式(I)的化合物特别是具有咔唑取代基的那些的合成方法在下述方案3中以一般形式示出。将咔唑基团(化合物G)经由Ullmann或Buchwald偶联导入其中的化合物中。此外,可以经由Suzuki偶联导入被咔唑或二芳基氨基取代的芳基(化合物H)。
方案3
本发明因此还提供了用于制备式(I)的化合物的方法,其特征在于,以偶联反应进一步转化式(Int-I)的化合物,
式(Int-I),
其中,在式(Int-I)的化合物中出现的可变基团和指数是如对于式(I)的化合物所定义的,并且在中央画有N的苯环中,一个以上环成员-CR1=在各情况下可以被-N=替换,并且其中Y是反应性基团。
此偶联反应优选是过渡金属催化的偶联反应,更优选Pd-或Cu催化的偶联反应。最优选的是Buchwald偶联或Ullmann偶联。偶联反应优选与芳基胺化合物或咔唑化合物的氮原子进行。
Y基团优选选自I、Br、Cl、O-甲苯磺酸酯、O-三氟甲磺酸酯、O-磺酸酯、硼酸、硼酸酯、部分氟化的硅烷基团和重氮基团。更优选地,Y基团选自I、Br和Cl。
本发明的上述化合物,特别是被反应性离去基团如溴、碘、氯、硼酸或硼酸酯取代的化合物,可以用作制备相应的低聚物、树枝状大分子或聚合物的单体。合适的反应性离去基团是例如溴、碘、氯、硼酸类、硼酸酯、胺、具有端部C-C双键或C-C三键的烯基或炔基、环氧乙烷类、环氧丙烷类、进入环加成例如1,3-偶极环加成的基团(例如二烯烃或叠氮物)、羧酸衍生物、醇和硅烷。
本发明因此还提供含有一种以上式(I)的化合物的低聚物、聚合物或树枝状大分子,其中结合到聚合物、低聚物或树枝状大分子的一个或多个键可以位于任何想要的在式(I)中被R1或R2取代的位置。根据式(I)的化合物的连接,该化合物是低聚物或聚合物的侧链的部分或主链的部分。在本发明的上下文中,理解低聚物表示由至少三个单体单元形成的化合物。在本发明的上下文中,理解聚合物表示由至少十个单体单元形成的化合物。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、支链的或树型的。在具有直链连接的结构中,式(I)的单元可以直接相互接合,或者它们可以经由二价基团例如经由取代的或未取代的亚烷基、经由杂原子或经由二价芳族或杂芳族基团相互接合。在支链的或树型的结构中,可以例如对于三个以上式(I)的单元,经由三价或更高价基团例如经由三价或更高价芳族或杂芳族接合,以得到支链的或树型的低聚物或聚合物。
对于低聚物、树枝状大分子和聚合物中的式(I)的重复单元,使用如上对于式(I)的化合物所述的相同优选内容。
为了制备低聚物或聚合物,将本发明的单体均聚或与另外的单体共聚。合适的且优选的共聚单体选自芴类(例如根据EP 842208或WO 00/22026)、螺环双芴类(例如根据EP707020、EP 894107或WO 06/061181)、对苯类(例如根据WO 1992/18552)、咔唑类(例如根据WO 04/070772或WO 2004/113468)、噻吩类(例如根据EP 1028136)、二氢菲类(例如根据WO2005/014689或WO 2007/006383)、顺式-和反式-茚并芴类(例如根据WO 2004/041901或WO2004/113412)、酮类(例如根据WO 2005/040302)、菲类(例如根据WO 2005/104264或WO2007/017066)或此外多个这些单元。聚合物、低聚物和树枝状大分子典型地还含有另外的单元,例如发射(荧光或磷光)单元,例如乙烯基三芳基胺(例如根据WO 2007/068325)或磷光金属配合物(例如根据WO 2006/003000),和/或电荷传输单元,尤其是基于三芳基胺的那些。
本发明的聚合物、低聚物和树枝状大分子具有有利的性质,特别是高寿命、高效率和良好的彩色坐标。
本发明的聚合物和低聚物通常通过一种以上单体类型的聚合制备,所述单体类型中至少一种单体导致聚合物中的式(I)的重复单元。合适的聚合反应对于本领域技术人员来说是已知的,并且描述在文献中。导致C-C和C-N键的特别合适的且优选的聚合反应如下:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合;和
(D)HARTWIG-BUCHWALD聚合。
怎样可以通过这些方法进行聚合以及随后怎样可以将聚合物从反应介质分离并纯化对于本领域技术人员来说是已知的,并且描述在文献中,例如WO 2003/048225、WO2004/037887和WO 2004/037887中。
为了从液相加工本发明的化合物,例如通过旋涂或通过印刷法,需要本发明的化合物的制剂。这些制剂可以是,例如溶液、分散液或乳液。为此目的,可以优选的是使用两种以上溶剂的混合物。合适的且优选的溶剂是,例如,甲苯、茴香醚、邻-、间-或对-二甲苯、苯甲酸甲酯、1,2,3,4-四氢化萘、藜芦醚、THF、甲基-THF、THP、氯苯、二烷、苯氧基甲苯,特别是3-苯氧基甲苯、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧乙醇、2-吡咯烷二酮、3-甲基茴香醚、4-甲基茴香醚、3,4-二甲基茴香醚、3,5-二甲基茴香醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、枯烯、环己醇、环己酮、环己基苯、萘烷、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、NMP、对-伞花烃、苯乙醚、1,4-二异丙基苯、二苄基醚、二甘醇丁基甲基醚、三甘醇丁基甲基醚、二甘醇二丁基醚、三甘醇二甲醚、二甘醇单丁醚、三丙二醇二甲醚、四甘醇二甲醚、2-异丙基萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-双(3,4-二甲基苯基)乙烷或这些溶剂的混合物。
本发明因此进一步提供一种制剂,特别是溶液、分散液或乳液,其包含至少一种式(I)的化合物或至少一种含有至少一种式(I)的单元的聚合物、低聚物或树枝状大分子和至少一种溶剂,优选有机溶剂。可以制备这种溶液的方法对于本领域技术人员来说是已知的,并且描述在例如WO 2002/072714、WO 2003/019694和其中引用的文献中。
本发明的化合物适合于在电子器件中特别是在有机电致发光器件(OLED)中使用。该化合物,取决于取代基等因素,可以用在不同的功能中和/或层中。优选地,化合物用作基体材料,更优选作为用于发射层中的磷光发射体的基体材料,或作为在空穴传输层中的空穴传输材料。在本发明的备选的实施方案中,该化合物也可以用作在电子传输层中的电子传输材料。
本发明进一步提供了式(I)的化合物在电子器件中的用途。这些电子器件优选选自由以下各项组成的组: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、有机感光器、有机场猝灭(field-quench)器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-激光)且更优选选自有机电致发光器件(OLED)。
本发明进一步提供一种电子器件,其包含阳极、阴极和至少一个有机层,其中有机层包含至少一种式(I)的化合物。此电子器件优选选自上述的器件且更优选是有机电致发光器件(OLED)。
除了阴极、阳极和发射层,有机电致发光器件可以还包含另外的层。这些在各情况下选自例如一个以上空穴注入层、空穴传输层、空穴阻挡体层、电子传输层、电子注入层、电子阻挡体层、激子阻挡体层、电荷产生层(IDMC 2003,Taiwan;Session 21OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,具有电荷产生层的多光子有机EL器件(Multiphoton Organic EL Device Having Charge GenerationLayer))、外耦合层和/或有机或无机p/n结。然而,应当指出,不是这些层中每一个都必须要存在,并且层的选择总是取决于所用的化合物并且特别地还取决于器件是荧光还是磷光电致发光器件。在特别的层和功能中优选使用的化合物清楚地公开在后续段落中。
在有机电致发光器件中的层的次序优选如下:
-阳极
-空穴注入层
-空穴传输层
-任选地1、2或3个另外的空穴传输层
-发射层
-电子传输层
-电子注入层
-阴极。
描述的层不必全部存在,和/或可以附加地存在另外的层。
本发明的有机电致发光器件可以含有两个以上发射层。更优选地,这些发射层在这种情况下总的具有若干个在380nm至750nm之间的发射最大值,使得总的结果是白色发射;换言之,多种可以是荧光物或磷光物并且发射蓝色或黄色或橙色或红色光的发射化合物用在发射层中。尤其优选的是三层系统,即具有三个发射层的系统,其中优选这些层中的至少一层包含至少一种式(I)的化合物,并且其中所述三层显示蓝色、绿色和橙色或红色发射(对于基础结构,参见例如WO 2005/011013)。备选地和/或附加地,本发明的化合物也可以存在于空穴传输层中或其他层中。
在根据本申请的发白光的OLED中,除了使用多个彩色发射的发射体化合物,也可以使用跨宽波长范围发射的单一发射体化合物。
根据本发明,当式(I)的化合物用在包含一种以上磷光发射体的电子器件中时,是优选的。在这种情况下,化合物可以用在不同的层中,优选在空穴传输层中或在发射层中。
根据本申请,术语“磷光发射体”包括如下化合物:其中光发射是通过自旋禁止的跃迁实现的,例如,从激发的三重态或具有更高自旋量子数的状态如五重态的跃迁。
合适的磷光发射体具体是当适当地受激时发光(优选在可见光区)的化合物,并且其含有至少一种原子数大于20、优选大于38、且小于84、更优选大于56且小于80的原子。作为磷光发射体,优选使用含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是含有铱、铂或铜的化合物。
在本发明的上下文中,所有发光的铱、铂或铜配合物都被认为是磷光化合物。
磷光发光体的实例可以在申请WO 2000/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 2005/033244、WO 2005/019373和US 2005/0258742中找到。通常,根据现有技术用于磷光OLED的且对于有机电致发光器件领域的技术人员来说已知的全部磷光配合物都适合用于本发明的器件。对于本领域技术人员来说,还可以在不运用发明性技艺的情况下,在OLED中与本发明的化合物组合使用另外的磷光配合物。合适的磷光发射体的进一步的实例可以在后面的段落中随附的列表中找到。
在本发明的一个优选的实施方案中,式(I)的化合物用作发射层中的基体材料,与一种以上荧光或磷光发射体(优选磷光发射体)组合。优选地,式(I)的化合物在这种情况下具有是单键的X基团,并且因此化合物含有咔唑基团。
在这种情况下在发射层中的基体材料的比例对于荧光发射层来说在50.0%至99.9%之间,优选在80.0%至99.5%之间,且更优选在92.0%至99.5%之间,并且对于磷光发射层来说在85.0%至97.0%之间。相应地,发射体的比例对于荧光发射层来说在0.1%至50.0%之间,优选在0.5%至20.0%之间,且更优选在0.5%至8.0%之间,并且对于磷光发射层来说在3.0%至15.0%之间。
理解以%表示的化合物的比例的图在其中化合物从气相施加的那些情况中的表示体积%,并且在其中化合物从液相施加的情况中表示重量%。
有机电致发光器件的发射层也可以包含含有多种基体材料(混合基体系统)和/或多种发射体的系统。在这种情况下,发射体通常也是那些在系统中具有较小比例的材料并且基体材料也是那些在系统中具有较大比例的材料。不过,在单独的情况下,在系统中的单一基体材料的比例可以小于单一发射体材料的比例。
在本发明的进一步优选的实施方案中,式(I)的化合物用作混合基体系统的组分。混合基体系统优选包括两种或三种不同的基体材料,更优选两种不同的基体材料。优选地在这种情况下,两种材料中的一种是具有空穴传输性质的材料,并且另一种材料是具有电子传输性质的材料。所述两种不同的基体材料可以以1∶50至1∶1、优选1∶20至1∶1、更优选1∶10至1∶1且最优选1∶4至1∶1的比率存在。优选在磷光有机电致发光器件中使用混合基体系统。关于混合基体系统的更多详细信息的一个来源是申请WO 2010/108579。
混合基体系统可以包含一种以上发射体化合物。根据本发明,发射体化合物一起占总混合物的0.1%至50.0%的比例,且优选总混合物的0.5%至20.0%的比例。相应地,基体化合物一起占总混合物的50.0%至99.9%的比例,且优选总混合物的80.0%至99.5%的比例。
特别地合适的可以与本发明的化合物组合使用作为混合基体系统的基体组分的基体材料选自下文对于磷光发射体规定的优选的基体材料或对荧光发射体规定的优选的基体材料,根据在混合基体系统中所用的发射体是什么类型。
用于包含本发明的化合物的混合基体系统中的优选的磷光发射体是列在后续表格中的磷光发射体。
在本发明的进一步优选的实施方案中,式(I)的化合物用作空穴传输材料。在该情况下,该化合物优选用在空穴传输层、电子阻挡体层或空穴注入层中。优选地,式(I)的化合物在这种情况下不具有任何X基团,表示化合物具有是芳基氨基的A基团。
根据本申请的空穴传输层是在阳极和发射层之间的具有空穴传输功能的层。
在本申请的上下文中,理解空穴注入层和电子阻挡体层是空穴传输层的特别的实施方案。在多个空穴传输层在阳极和发射层之间的情况下,空穴注入层是直接邻接阳极的或仅由单个阳极涂层与其分开的空穴传输层。在多个空穴传输层在阳极和发射层之间的情况下,电子阻挡体层是在阳极侧直接邻接发射层的空穴传输层。
如果式(I)的化合物用作空穴传输层、空穴注入层或电子阻挡体层中的空穴传输材料,该化合物可以以纯材料即100%的比例用在空穴传输层中,或者它可以与一种以上另外的化合物组合使用。在一个优选的实施方案中,含有式(I)的化合物的有机层随后附加地含有一种以上p-掺杂剂。根据本发明使用的p-掺杂剂优选是那些能够氧化在混合物中的其他化合物中的一种或多种的有机电子受体化合物。
p-掺杂剂的特别优选的实施方案是在WO 2011/073149、EP 1968131、EP 2276085、EP 2213662、EP 1722602、EP 2045848、DE 102007031220、US 8044390、US 8057712、WO 2009/003455、WO 2010/094378、WO 2011/120709、US 2010/0096600和WO 2012/095143中公开的化合物。
特别优选的p-掺杂剂是:喹啉并二甲烷化合物,氮杂茚并芴二酮类,氮杂非那烯类,氮杂三亚苯类,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者第3主族的金属的金属氧化物,和过渡金属配合物,优选Cu、Co、Ni、Pd和Pt与含有至少一个氧原子作为键合位点的配体的配合物。更优选的是过渡金属氧化物作为掺杂剂,优选铼、钼和钨的氧化物,更优选Re2O7、MoO3、WO3和ReO3。
p-掺杂剂优选基本上均匀分布在p-掺杂层中。这可以例如通过p-掺杂剂和空穴传输材料基体的共蒸发完成这一分布。
在本发明的进一步的实施方案中,式(I)的化合物用作在电子传输层或电子注入层或空穴阻挡体层中的电子传输材料。对于此目的,优选的是式(I)的化合物具有是单键的X基团,使得化合物含有咔唑基团。优选地,该化合物在此用途的情况下,附加地含有一种以上拉电子基团,例如缺电子的杂芳基,如嘧啶基、三嗪基或苯并咪唑基。
优选地在本发明的电子器件中使用的另外的功能材料在下文中详述。
在下表中列出的化合物是特别合适的磷光发射体。
优选的荧光发射体选自芳基胺的类别。在本发明的上下文中,理解芳基胺表示含有三个直接键合至氮的取代的或未取代的芳族或杂芳族环体系的化合物。优选地,这些芳族或杂芳族环体系中的至少一个是稠合的环体系,更优选具有至少14个芳族环原子。这些的优选实例是芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族胺或芳族二胺。理解芳族蒽胺表示其中二芳基氨基直接键合至蒽基团的化合物,优选在9位键合。理解芳族蒽二胺表示其中两个二芳基氨基直接键合至蒽基团的化合物,优选在9、10位键合。类似地定义芳族芘胺、芘二胺、胺或二胺,其中二芳基氨基优选在1位或1、6位键合至芘。进一步优选的发射体是茚并芴胺或-芴二胺,例如根据WO 2006/108497或WO 2006/122630的,苯并茚并芴胺或-芴二胺,例如根据WO 2008/006449的,和二苯并茚并芴胺或-芴二胺,例如根据WO 2007/140847的,以及在WO 2010/012328中公开的具有稠合芳基的茚并芴衍生物。同样优选的是在WO 2012/048780和尚未公布的EP 12004426.8中公开的芘芳基胺。同样优选的是在尚未公布的EP 12006239.3中公开的苯并茚并芴胺和在尚未公布的EP 13000012.8中公开的苯并芴胺。
随着本发明的化合物优选用于荧光发射体的可用的基体材料是来自各种物质类别的材料。优选的基体材料选自寡聚亚芳基(例如根据EP 676461的2,2‘,7,7‘-四苯基螺环双芴,或二萘基蒽)的类别,特别是含有稠合芳族基团的寡聚亚芳基的类别,寡聚亚芳基乙亚烯基(例如根据EP 676461的DPVBi或螺环-DPVBi),多肢(polypodal)金属配合物(例如根据WO 2004/081017),空穴传导化合物(例如根据WO 2004/058911),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),阻转异构体(例如根据WO 2006/048268),硼酸衍生物(例如根据WO 2006/117052)或苯并蒽(例如根据WO 2008/145239)。特别优选的基体材料选自包含萘、蒽、苯并蒽和/或芘的寡聚亚芳基的类别或这些化合物的阻转异构体,寡聚亚芳基乙亚烯基,酮,氧化膦和亚砜。非常特别优选的基体材料选自包含蒽、苯并蒽、苯并菲和/或芘的寡聚亚芳基的类别或这些化合物的阻转异构体。在本发明的上下文中,应当理解寡聚亚芳基表示其中至少三个芳基或亚芳基相互键合的化合物。更优选的是在WO 2006/097208、WO 2006/131192、WO 2007/065550、WO 2007/110129、WO2007/065678、WO 2008/145239、WO 2009/100925、WO 2011/054442和EP 1553154中公开的蒽衍生物,和在EP 1749809、EP 1905754和US 2012/0187826中公开的芘化合物。
随着本发明的化合物用于磷光发射体的优选的基体材料是芳族胺,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-双咔唑联苯)或根据WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851的化合物,桥联的咔唑衍生物,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、EP 1617711、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,寡聚亚苯基,偶极基体材料,例如根据WO 2007/137725的,硅烷,例如根据WO 2005/111172的,氮杂硼杂环戊二烯类(azaborole)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,锌配合物,例如根据EP 652273或WO 2009/062578的,铝配合物,例如BAlq、二氮杂噻咯衍生物和四氮杂噻咯衍生物,例如根据WO 2010/054729的,二氮杂磷杂环戊二烯(diazaphosphole)衍生物,例如根据WO 2010/054730的,和铝配合物,例如BAlQ。
正如随着本发明的化合物用在本发明的空穴注入或空穴传输层或电子阻挡剂层中或电子传输层中的,合适的电荷传输材料是例如在Y.Shirota等,Chem.Rev.2007,107(4),953-1010中公开的化合物,或根据现有技术在这些层中使用的其他材料。
用于电子传输层的材料可以是任何根据如现有技术作为电子传输层中的电子传输材料使用的材料。特别合适的是铝配合物,例如Alq3,锆配合物,例如Zrq4,锂配合物,例如Liq,苯并咪唑衍生物,三嗪衍生物,嘧啶衍生物,吡啶衍生物,吡嗪衍生物,喹喔啉衍生物,喹啉衍生物,二唑衍生物,芳族酮,内酰胺,甲硼烷,二氮杂磷杂环戊二烯衍生物和氧化膦衍生物。其他合适的材料是上述化合物的衍生物,如在JP 2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975和WO 2010/072300中公开的。
有机电致发光器件的优选的阴极是具有低功函数的金属、由多种金属例如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)构成的金属合金或多层结构。附加地合适的是由碱金属或碱土金属与银构成的合金,例如由镁和银构成的合金。在多层结构的情况下,除了提到的金属,也可以使用其他具有比较高功函数的金属,例如Ag或Al,在该情况下通常使用例如金属的组合如Ca/Ag、Mg/Ag或Ba/Ag。还优选可以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。为此目的可用的材料的实例是碱金属或碱土金属氟化物,但也是相应的氧化物或碳酸盐(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3等)。为此目的还可以使用喹啉酸锂(LiQ)。此层的层厚优选在0.5和5nm之间。
优选的阳极是具有高功函数的材料。优选地,阳极具有对真空大于4.5eV的功函数。首先,具有高氧化还原电势的金属适用于此目的,例如Ag、Pt或Au。其次,金属/金属氧化物电极(例如Al/Ni/NiOx、Al/PtOx)也可以是优选的。对于某些应用,电极中的至少一个是透明的或部分透明的,以使得有机材料的辐射(有机太阳能电池)或光的发射(OLED、O-激光)成为可能。此处优选的阳极材料是导电的混合金属氧化物。特别优选的是氧化铟锡(ITO)或氧化铟锌(IZO)。还优选的是导电的掺杂的有机材料,特别是导电的掺杂的聚合物。此外,阳极也可以由两个以上层组成,例如,由ITO的内层和金属氧化物(优选氧化钨、氧化钼或氧化钒)的外层组成。
适当地将器件(根据应用)结构化、连接触点和最终密封,因为在水和/或空气的存在下缩短本发明的器件的寿命。
在一个优选的实施方案中,本发明的有机电致发光器件的特征在于通过升华过程覆盖一个或多个层。在这种情况下,通过在真空升华系统中,在小于10-5毫巴、优选小于10-6毫巴的初始压力下气相沉积,来涂敷材料。然而,在这种情况下,也可以在甚至更低例如小于10-7毫巴的初始压力下。
同样,优选的有机电致发光器件特征在于通过OVPD(有机气相沉积)方法或借助负载气体升华对一个或多个层覆层。在这种情况下,在10-5毫巴至1巴之间的压力下涂敷材料。此方法的一种具体情况是OVJP(有机蒸气喷墨打印)方法,其中通过喷头直接将材料涂敷并因此结构化(例如,M.S.Arnold等,Appl.Phys.Lett.2008,92,053301)。
此外,另外优选的有机电致发光器件的特征在于由溶液制备一个或多个层,例如通过旋涂,或通过任何印刷方法,例如丝网印刷、柔性版印刷、喷嘴印刷或胶版印刷,但更优选LITI(光感应热成像,热转移印刷)或喷墨打印。为此目的,需要可溶性的式(I)的化合物。可以通过化合物的合适的取代,得到高溶解度。
还优选的是,通过涂敷来自溶液的一个或多个层并且通过升华方法涂敷一个或多个层,制备本发明的有机电致发光器件。
根据本发明,包含一种或多种式(I)的化合物的电子器件可以用于显示器中、作为照明应用的光源和作为医疗和/或化妆应用(例如光疗法)中的光源。
工作例
以下的工作例用于解释本发明。不应当以限制的方式解释它们。
A)合成例
起始化合物10-溴苯并[h]喹啉从文献已知(CAS号[152583-10-3])。作为另外的起始化合物的相应的N-杂环衍生物由CAS[66693-82-1]已知。
苯并[h]喹啉-10-基(联苯-4-基)(9,9-二甲基-9H-芴-2-基)胺
将27.1g的联苯-4-基(9,9-二甲基-9H-芴-2-基)胺(75mmol)和19.4g的10-溴苯并[h]喹啉(75mmol)溶解在500mL的甲苯中。将溶液脱气并且用N2饱和。随后,将3.0mL(3.0mmol)的三叔丁基膦溶液和0.33g(1.52mmol)的乙酸钯(II)加入其中。随后,加入11.2g的叔丁醇钠(116mmol)。将反应混合物在保护气氛下加热至沸腾5h。随后将混合物在甲苯和水之间分配,并且将有机相用水洗涤两次并经过Na2SO4干燥并通过旋转蒸发进行浓缩。在将粗制产物用甲苯经过硅胶过滤后,将剩余的残余物从庚烷/甲苯再结晶并且最终在高真空下升华。纯度为99.9%;收率为28.3g(理论的70%)。
以类似的方式,制备以下化合物:
实施例2-1:
(4-苯并[h]喹啉-10-基苯基)联苯-4-基(9,9-二甲基-9H-芴-2-基)胺
将15.47g(75mmol)的4-溴苯硼酸、19.4g的10-溴苯并[h]喹啉(75mmol)和110mL的2M的含有NaHCO3-的水溶液(163mmol)悬浮在500mL的二甲氧基乙烷中。向此悬浮液中加入3.0g(3.45mmol)的四(三苯基膦)钯(0),并且将反应混合物在回流下加热22h。冷却之后,移除有机相,经过硅胶过滤,用400mL的水洗涤四次,并且随后浓缩至干燥。在将粗制产物用庚烷/甲苯(10∶1)经过硅胶过滤后,获得39g(71%)的10-(4-溴苯基)苯并[h]喹啉。
以类似的方式,制备以下化合物:
实施例3-1:
(4-苯并[h]喹啉-10-基苯基)联苯-4-基(9,9-二甲基-9H-芴-2-基)胺
将16.27g的联苯-2-基(9,9-二甲基-9H-芴-2-基)胺(45mmol)和15.0g的来自实施例2-1的产物(45mol)溶解在300mL的甲苯中。将溶液脱气并且用N2饱和。随后,将2.4g(2.9mmol)的三叔丁基膦溶液和0.20g(0.9mmol)的乙酸钯(II)加入其中。随后,加入6.68g的叔丁醇钠(67.5mmol)。将反应混合物在保护气氛下加热至沸腾16h。随后将混合物在甲苯和水之间分配,并且将有机相用水洗涤三次,并经过Na2SO4过滤,并通过旋转蒸发进行浓缩。在将粗制产物用甲苯经过硅胶过滤后,将剩余的残余物从庚烷/甲苯再结晶并且最终在高真空下升华。纯度为99.9%。收率为20g(理论的60%)。
以类似的方式,制备以下化合物:
实施例4-1:
10-苯并[h]喹啉-10-基-12,12-二甲基-10,12-二氢-10-氮杂茚并[2,1-b]芴
首先将30g(116mmol)的10-溴苯并[h]喹啉、32g(116mmol)的2,12-二甲基-10-苯基-10,12-二氢-10-氮杂茚并[2,1-b]芴、32g(232mmol)的碳酸钾、2.6g(11.6mmol)的1,3-二(2-吡啶基)-1,3-丙烷二酮和2.2(11.6mmol)的碘化铜充入1000mL的DMF中。将溶液脱气,用N2饱和,并且加热至100℃60h。随后,加入水和甲苯,将相分离,并且将有机相用水洗涤两次并经过Na2SO4干燥,并通过旋转蒸发进行浓缩。在将粗制产物用甲苯经过硅胶过滤后,将剩余的残余物从庚烷/甲苯再结晶并且最终在高真空下升华。纯度为99.9%。收率为37g(理论的71%)。
以类似的方式,制备以下化合物:
类似地,用58mmol的咔唑衍生物制备以下化合物:
B)器件例
通过根据WO 04/058911的通用方法制备本发明的OLED和根据现有技术的OLED,使该方法适合于本文描述的情况(层厚、材料的变化)。
在本发明的实施例I1至I6中和在随后的参照例C1中,有各种OLED的数据。所用的基板是涂布了厚度为50nm的结构化的ITO(氧化铟锡)的玻璃板。OLED基本上具有以下层结构:基板/p-掺杂的空穴传输层HIL1/空穴传输层HTL/p-掺杂的空穴传输层HIL2/空穴传输层EBL/发射层EML/电子传输层ETL/电子注入层EIL以及最后是阴极。阴极通过厚度为100nm的铝层形成。制备OLED所需的材料示于表1中,并且制得的各种电子器件示于表2中。
所有材料都在真空室中通过热气相沉积涂敷。在这种情况下发射层总是由至少一种基体材料(主体材料)和发光掺杂剂(发射体)组成,所述发光掺杂剂通过共蒸发以特定的体积比例加入一种或多种基体材料中。在本文中以H1∶TEG(10%)的形式给出的细节表示材料H1以90%的体积比例存在于层中,且TEG以10%的比例。以相似的方式,电子传输层或空穴注入层也可以由两种材料的混合物组成。
以标准方式表征OLED的特征。为此目的,从假设为Lambertian发光特性的电流-电压-发光特性(IUL特性),计算作为亮度的函数的电致发光光谱、电流效率(以cd/A测量)、功率效率(以lm/W测量)和外部量子效率(EQE,以百分比测量),并且也测定寿命。在1000cd/m2的亮度测定电致发光光谱,并且由其计算CIE 1931x和y颜色坐标。参数EQE@2mA/cm2指的是在电流密度为2mA/cm2时的外部量子效率。按小时报告的LD80@10 000cd/m2是OLED以恒电流降至初始强度的80%即降至8000cd/m2时的时间。
下面的实施例显示了本发明的化合物HTM1至HTM6在磷光OLED中作为空穴传输材料的用途。发射层由作为发射体材料的TEG1和作为基体材料的H1形成。
器件实施例1和2
制备绿色磷光参考器件C1,并且与本发明的器件I1和I2比较。参考器件C1在2mA/cm2的电流密度下具有11.7%的外部量子效率和90h的寿命(LD80@10 000cd/m2)。通过比较,本发明的器件I1具有为15.5%的更好的外部量子效率和为120h的更好的在10 000cd/m2的LD80。本发明的器件I2具有15.8%的量子效率和100h的寿命。
器件实施例3至6
制备绿色磷光参考器件C1,并且与本发明的器件I3至I6比较。参考器件C1在2mA/cm2的电流密度下具有11.7%的外部量子效率。相比之下,本发明的器件I3-I6具有为13.3%(I3)、14.2%(I4)、13.7%(I5)和12.8%(I6)的更好的外部量子效率。
实施例显示,本发明的化合物非常适合用于OLED,特别是用作空穴传输材料。然而,用途不限于此功能。该材料也适合用作例如发射层中的基体材料。
Claims (11)
1.式(I-1)和(I-2)的化合物
其中:
A选自式(A-1)的基团
所述基团经由用*标记的键结合,
Ar1在各个情况下是相同或不同的,并且选自苯和芴,其中每个可以被一个以上R1基团取代;
Ar2在各个情况下是相同或不同的,并且选自苯、联苯、三联苯、四联苯、芴、螺环双芴、咔唑、二苯并呋喃和二苯并噻吩,其中每个可以被一个以上R1基团取代;
X在各个情况下是相同或不同的,并且是单键或C(R2)2;
R1、R2在各个情况下是相同或不同的,并且是H、D、F、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3,具有1至20个碳原子的直链烷基或烷氧基、或者具有3至20个碳原子的支链的或环状的烷基或烷氧基、或者具有2至20个碳原子的烯基或炔基,其中上述基团可以各自被一个以上R3基团取代并且其中在上述基团中的一个以上CH2基团可以被-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2替换,或具有5至30个芳族环原子并可以被一个以上R3基团取代的芳族或杂芳族环体系;
R3在各个情况下是相同或不同的,并且是H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4,具有1至20个碳原子的直链烷基或烷氧基、或者具有3至20个碳原子的支链的或环状的烷基或烷氧基、或者具有2至20个碳原子的烯基或炔基,其中上述基团可以各自被一个以上R4基团取代并且其中在上述基团中的一个以上CH2基团可以被-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-O-、-S-、SO或SO2替换,或具有5至30个芳族环原子并可以被一个以上R4基团取代的芳族或杂芳族环体系;
R4在各个情况下是相同或不同的,并且是H、D、F、CN或具有1至20个碳原子的脂族、芳族或杂芳族有机基团,其中一个以上氢原子也可以被D、F或CN替换;
n是0、1或2;
i在各个情况下是相同或不同的,并且是0或1;
并且
所述式(I)的化合物不具有任何具有大于10个芳族环原子的稠合芳基或杂芳基作为取代基R1、R2、R3和R4。
2.根据权利要求1中所述的化合物,其特征在于,n是0。
3.根据权利要求1或2中所述的化合物,其特征在于,它不具有除所述A基团之外的任何另外的芳基氨基、任何另外的桥联的芳基氨基或任何另外的咔唑基团。
4.根据权利要求1或2中所述的化合物,其特征在于,它对应于式(I-1):
其中出现的基团和指数如在权利要求1至3的任意一项中所定义。
5.一种用于制备根据权利要求1至4的任意一项中所述的化合物的方法,其特征在于以偶联反应进一步转化式(Int-I-1)和(Int-I-2)的化合物:
其中出现的可变的基团和指数如在权利要求1至4的任意一项中对于式(I-1)和(I-2)的化合物所定义,并且其中Y是任何反应性基团。
6.一种低聚物、聚合物或树枝状大分子,所述低聚物、聚合物或树枝状大分子含有一种以上如在权利要求1至4的任意一项中所述的化合物,其中结合到所述聚合物、低聚物或树枝状大分子的键可以位于任何想要的在式(I-1)和(I-2)中被R1或R2取代的位置。
7.一种制剂,所述制剂包含至少一种如在权利要求1至4的任意一项中所述的化合物和至少一种溶剂。
8.根据在权利要求1至4的任意一项所述的化合物在电子器件中的用途。
9.一种电子器件,所述电子器件包括阳极、阴极和至少一个有机层,其中所述有机层包含至少一种如在权利要求1至4的任意一项中所述的化合物。
10.根据权利要求9中所述的电子器件,其特征在于,它选自由以下各项组成的组:有机集成电路、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机太阳能电池、有机光学检测器、有机感光器、有机场猝灭器件、有机发光电化学池、有机激光二极管和有机电致发光器件。
11.根据权利要求10中所述的有机电致发光器件,其特征在于,如在权利要求1至4的任意一项中所述的化合物在发射层中作为基体材料存在或在空穴传输层中作为空穴传输材料存在。
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KR102299572B1 (ko) | 2021-09-07 |
US10407394B2 (en) | 2019-09-10 |
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