JP5666483B2 - アザボロール配位子を有する金属錯体及び当該錯体を有する電子デバイス - Google Patents
アザボロール配位子を有する金属錯体及び当該錯体を有する電子デバイス Download PDFInfo
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- JP5666483B2 JP5666483B2 JP2011552336A JP2011552336A JP5666483B2 JP 5666483 B2 JP5666483 B2 JP 5666483B2 JP 2011552336 A JP2011552336 A JP 2011552336A JP 2011552336 A JP2011552336 A JP 2011552336A JP 5666483 B2 JP5666483 B2 JP 5666483B2
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- 150000004696 coordination complex Chemical class 0.000 title description 7
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- 125000003118 aryl group Chemical group 0.000 claims description 76
- 229910052751 metal Inorganic materials 0.000 claims description 54
- 239000002184 metal Substances 0.000 claims description 54
- -1 NR 2 Inorganic materials 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 27
- 239000011159 matrix material Substances 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
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- 230000000903 blocking effect Effects 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
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- 239000010948 rhodium Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
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- 238000007740 vapor deposition Methods 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 3
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 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 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- PMZLFYBZWYRRAZ-UHFFFAOYSA-N tricyclohexylarsane Chemical compound C1CCCCC1[As](C1CCCCC1)C1CCCCC1 PMZLFYBZWYRRAZ-UHFFFAOYSA-N 0.000 description 2
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- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
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- NMFOJQOMUJFKND-BYPYZUCNSA-N (2S)-2-[bis(methylamino)amino]propanoic acid Chemical compound CNN(NC)[C@@H](C)C(O)=O NMFOJQOMUJFKND-BYPYZUCNSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N salicylic acid phenyl ester Natural products OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000004332 silver 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
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 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
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000006836 terphenylene group Chemical group 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
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 description 1
- UTLODFUDVKXUIW-UHFFFAOYSA-N tert-butyl(2-tert-butylphosphanylpropan-2-yl)phosphane Chemical compound C(C)(C)(C)PC(C)(C)PC(C)(C)C UTLODFUDVKXUIW-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- QZBJYTDDWVXFDF-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)arsane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[As](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QZBJYTDDWVXFDF-UHFFFAOYSA-N 0.000 description 1
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- QYWFCUVQKBNIRJ-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)stibane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Sb](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QYWFCUVQKBNIRJ-UHFFFAOYSA-N 0.000 description 1
- YSPBORFVJLIOMX-UHFFFAOYSA-N tritert-butylarsane Chemical compound CC(C)(C)[As](C(C)(C)C)C(C)(C)C YSPBORFVJLIOMX-UHFFFAOYSA-N 0.000 description 1
- NZJQTVDLVPHKGY-UHFFFAOYSA-N tritert-butylstibane Chemical compound CC(C)(C)[Sb](C(C)(C)C)C(C)(C)C NZJQTVDLVPHKGY-UHFFFAOYSA-N 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
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
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Description
Yは、出現毎に、各々の場合において、互いに独立して、NR3、O又はSであり;
Xは、出現毎に、各々の場合において、互いに独立して、CR1又はNであり;
R1は、出現毎に、各々の場合において、互いに独立して、H、D、F、Cl、Br、I、CHO、N(R2)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR2=C(R2)2、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、2〜40のC原子を有する直鎖アルケニル若しくはアルキニル基又は3〜40のC原子を有する分枝若しくは環状アルキル、アルケニル、アルキニル、アルコキシ若しくはチオアルコキシ基であって、それらの各々は、1以上の基R2により置換されていてもよく、1以上の非隣接CH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S若しくはCONR2により置き換えられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CN若しくはNO2により置き換えられていてもよいものであるか、5〜60の芳香環原子を有する芳香族若しくは芳香族複素環であって、各々の場合において、1以上の基R2により置換されていてもよいものであるか、5〜60の芳香環原子を有するアリールオキシ若しくはヘテロアリールオキシ基であって、1以上の基R2により置換されていてもよいものであるか、或いはこれらの系の組合せであり、2以上の隣接する置換基R1は単環又は多環の脂肪族若しくは芳香族環系を互いに形成していてもよく;
R2は、出現毎に、各々の場合において、互いに独立して、H、D、F又は1〜20のC原子を有する脂肪族、芳香族及び/又は芳香族複素炭化水素基であって、更に、1以上のH原子がFにより置き換えられていてもよいものであり;ここで、2以上の置換基R2は、単環又は多環の脂肪族若しくは芳香族環系を互いに形成していてもよく;
R3は、出現毎に、各々の場合において、互いに独立して、H、D、1〜20のC原子を有する脂肪族炭化水素基又は5〜30の芳香環原子を有する芳香族若しくは芳香族複素環系であって、1以上の基R1により置換されていてもよいものであるか;或いは、R3は、R3が、荷電又は非荷電の環外若しくは環内ドナー原子Dを介して金属Mに結合している配位基であり;
ここで、複数の部分配位子(part-ligand)Lは、互いに、或いはLとL’及び/又はL’’とが共に、任意にR3を介した連結によって多座若しくは多脚型配位子を形成していてもよく;
Arは、出現毎に、各々の場合において、互いに独立して、5〜30の芳香環原子を有する芳香族又は芳香族複素環系であって、1以上の非芳香族基R1により置換されていてもよいものであり;
L’、L’’は、いずれかの望まれる共配位子であり;
さらに、Mが配位数6の場合、n=1〜6(1,2,3,4,5,6)、o=0〜5(0,1,2,3,4,5)及びm=0〜5(0,1,2,3,4,5)であり、Mが配位数5の場合、n=1〜5(1,2,3,4,5)、o=0〜4(0,1,2,3,4)及びm=0〜4(0,1,2,3,4)であり、Mが配位数4の場合、n=1〜4(1,2,3,4)、m=0〜3(0,1,2,3)及びo=0〜3(0,1,2,3)である。
D2は、出現毎に、各々の場合において、互いに独立して、O、S、NR1、N(R1)2、PR1、P(R1)2、P(O)R1、P(O)(R1)2、AsR1、As(R1)2、As(O)R1、As(O)(R1)2、SbR1、Sb(R1)2、Sb(O)R1、Sb(O)(R1)2、BiR1、Bi(R1)2、Bi(O)R1、Bi(O)(R1)2、OR1、SR1、SeR1及びTeR1からなる群より選択される環外ドナー基であり;
X1は、出現毎に、各々の場合において、互いに独立して、C又はNであり;
Cy1は、出現毎に、各々の場合において、互いに独立して、5〜30の環原子を有する芳香族若しくは芳香族複素環基又は芳香環系若しくは芳香族複素環系であって、X1及びD1は、当該芳香族若しくは芳香族複素環基又は当該芳香族若しくは芳香族複素環系において存在しないか、或いはD2が環外の基として結合しているものである。
Halは、出現毎に、同じであるか又は異なり、F、Cl、Br又はIであり;
Ligは、出現毎に、同じであるか又は異なり、中性又はモノアニオン性の単座配位子若しくは二座配位子、例えば、ハロゲン化物、ヒドロキシド又はエチレングリコレートであり;
qは、出現毎に、同じであるか又は異なり、0、1、2、3又は4であり、好ましくは、0、1又は2であり;
rは、出現毎に、同じであるか又は異なり、1、2、3、4、5又は6であり;
ここで、式(48)及び(49)の化合物は、帯電していてもよく、1以上の対イオンを含んでいてもよく;さらに、式(47)乃至(49)、特に、式(49)の化合物は、水和物の形態であってもよい。
Yは、出現毎に、各々の場合において、互いに独立して、NR3、O又はSであり;
Xは、出現毎に、各々の場合において、互いに独立して、CR1又はNであり;
R1は、出現毎に、各々の場合において、互いに独立して、H、D、F、Cl、Br、I、CHO、N(R2)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR2=C(R2)2、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ又は2〜40のC原子を有する直鎖アルケニル若しくはアルキニル基若しくは3〜40のC原子を有する分枝若しくは環状のアルキル、アルケニル、アルキニル、アルコキシ若しくはチオアルコキシ基であって、それらの各々は、1以上の基R2により置換されていてもよく、1以上の非隣接CH2基は、by R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S又はCONR2により置き換えられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CN又はNO2により置き換えられているものであるか、5〜60の芳香環原子を有する芳香族又は芳香族複素環系であって、1以上の基R2により置換されていてもよいものであるか、5〜60の芳香環原子を有するアリールオキシ又はヘテロアリールオキシ基であって、1以上の基R2により置換されていてもよいものであるか、或いはこれらの系の組合せであり、2以上の隣接する置換基R1は、単環又は多環の脂肪族若しくは芳香環系を互いに形成していてもよく;
R2は、出現毎に、各々の場合において、互いに独立して、H、D、F又は1〜20のC原子を有する脂肪族、芳香族及び/又は芳香族複素環炭化水素基であって、更に、1以上のH原子は、Fによって置き換えられていてもよいものであり;ここで、2以上の置換基R2は、単環又は多環の脂肪族若しくは芳香環系を互いに形成していてもよく;
R3は、出現毎に、各々の場合において、互いに独立して、1〜20のC原子を有する脂肪族炭化水素基又は5〜30の芳香環原子を有する芳香族若しくは芳香族複素環系であって、更に、1以上のH原子は、R1によって置き換えられていてもよいものであり、少なくとも1つの基R3が、金属Mに結合する荷電又は非荷電の環外若しくは環内ドナー原子Dを含んだ配位基を示すことを特徴とし;
ここで、複数の部分配位子Lは、多座又は多脚型配位子を、互いに若しくはLとL’及び/又はL’’とが共に、任意にR3を介した連結によって形成してもよく;
Arは、出現毎に、各々の場合において、互いに独立して、5〜30の芳香環原子を有する芳香族又は芳香族複素環系であって、非芳香族基R1により置換されていてもよいものであり;
さらに、Mが配位数6を有する場合、n=1〜6(1,2,3,4,5,6)、o=0〜5(0,1,2,3,4,5)及びm=0〜5(0,1,2,3,4,5)であり、Mが配位数5を有する場合、n=1〜5(1,2,3,4,5)、o=0〜4(0,1,2,3,4)及びm=0〜4(0,1,2,3,4)であり、Mが配位数4を有する場合、n=1〜4(1,2,3,4)、m=0〜3(0,1,2,3)及びo=0〜3(0,1,2,3)である。
以下の合成は、他に示さない限り、乾燥溶媒中、保護ガス環境下行われる。溶媒及び試薬は、ALDRICH又はABCRから購入され得る。
以下に示す対称型N,N’−置換o−フェレンジアミンは、o−ジブロモベンゼン及び対応するアミンから、Tetrahedron Letters 2004,45,6851−6853と同様に調製される。
以下に示す非対称型N,N’置換o−フェニレンジアミンは、臭化物及びアミンから、Organometallics 2009,28,5244−5252と同様に調製される。
以下に示す2−ブロモベンゾ−1,3,2−ジアザボロールは、対応するN,N’−置換o−フェニレンジアミンから、三臭化ホウ素との反応によりJ.Org.Chem.1962,27,4701−4702と同様に調製される。
以下に示す2−ブロモ−1,3,2−ジアザボロールは、対応するジイミンからマグネシウムを使用した還元及び続く三臭化ホウ素との反応によりScience 2006,314,113−116と同様に調製される。
以下に示す2−ブロモ−1,3,2−ジアザボロリジンは、対応するジアミンから、三臭化ホウ素/トリエチルアミン付加体との反応により、Organometallics 2005,24,5455−5463と同様に調製される。
化合物1の合成:
2−ブロモ−1,3−ジピリジン−2−イル−1,3,2−ジアザボロリジン910.4mg(3mmol)及びナフタレン76.7mg(0.6mmol)のTHF溶液50mlを−45℃まで冷却する。リチウム粉末209.2mg(30mmol)を添加し、混合物を冷却しながら24時間攪拌し、続いてセルライトにより濾過する。濾液を三塩化トリスピリジノイリジウム537.4mg(1.0mmol)のTHF溶液25mlに滴下し、−45℃に冷却し、冷却をやめ、混合物を室温で5時間攪拌する。揮発性の構成成分をロータリーエバポレータで除去し、残渣を暖かいヘプタン250mlに懸濁する。セルライトにより濾過した後、揮発性の構成成分をロータリーエバポレータで除去し、残渣をトルエンから4回再結晶させる。収率:42%(363.1mg、0.4mmol)。
本発明に従うエレクトロルミネセンスデバイスは、例えば、WO05/003253に記載される通り製造され得る。種々のOLEDの結果がここで比較される。より良好な比較のため、その基本的構造、使用される材料、ドーピングの程度及び層の厚さは、同一である。
正孔注入層(HIL) 20nmの2,2’,7,7’−テトラキス(ジ−パラ−トリルアミノ)スピロ−9,9’−ビフルオレン
正孔輸送層(HTL) 5nmのNPB(N−ナフチル−N−フェニル−4,4’−ジアミノビフェニル)
電子ブロッキング層(EBL) 15nmのEBL(9,9−ビス−(3,5−ジフェニルアミノフェニル)フルオレン)
発光層(EML) 40nmのホスト材料:ビス−[1,3’;1’,1’’;3’’,1’’’;3’’’,1’’’’]キンキフェニル−5’’−イルメタノン(M)
ドーパント:体積%ドーピング;化合物表1を参照
正孔ブロッキング層(HBL) 10nm:ビス−[1,3’;1’,1’’;3’’,1’’’;3’’’,1’’’’]キノキフェニル−5’’−イルメタノン(M)
電子伝導体(ETL) 20nmのAlQ3(トリス(キノリナート)アルミニウム(III))
カソード 1nmのLiF、上部に100nmのAl。
Claims (13)
- 一般式Iの化合物を含んだ電子デバイスであって、
Yは、各々の場合において、互いに独立して、NR3、O又はSであり;
Xは、各々の場合において、互いに独立して、CR1又はNであり;
R1は、各々の場合において、互いに独立して、H、D、F、Cl、Br、I、CHO、N(R2)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR2=C(R2)2、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、2〜40のC原子を有する直鎖アルケニル若しくはアルキニル基又は3〜40のC原子を有する分枝若しくは環状アルキル、アルケニル、アルキニル、アルコキシ若しくはチオアルコキシ基であって、それらの各々は、1以上の基R2により置換されていてもよく、1以上の非隣接CH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S又はCONR2により置き換えられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CN又はNO2により置き換えられていてもよいものであるか、5〜60の芳香環原子を有する芳香族又は芳香族複素環系であって、各々の場合において、1以上の基R2により置換されていてもよいものであるか、5〜60の芳香環原子を有するアリールオキシ又はヘテロアリールオキシ基であって、1以上の基R2により置換されていてもよいものであるか、或いはこれらの系の組合せであり、2以上の隣接する置換基R1は、単環又は多環の脂肪族若しくは芳香環系を互いに形成していてもよく;
R2は、各々の場合において、互いに独立して、H、D、F又は1〜20のC原子を有する脂肪族、芳香族及び/又は芳香族複素炭化水素基であって、更に、1以上のH原子はFにより置き換えられていてもよいものであり;ここで、2以上の置換基R2は、単環又は多環の脂肪族若しくは芳香環系を互いに形成していてもよく;
Arは、各々の場合において、互いに独立して、5〜30の芳香環原子を有する芳香族又は芳香族複素環系であって、1以上の非芳香族基R1により置換されていてもよいものであり;
L’,L’’は、いずれかの望まれる共配位子であり;
更に、Mが配位数6を有する場合、n=1〜6(1,2,3,4,5,6)、o=0〜5(0,1,2,3,4,5)及びm=0〜5(0,1,2,3,4,5)であり、Mが配位数5を有する場合、n=1〜5(1,2,3,4,5)、o=0〜4(0,1,2,3,4)及びm=0〜4(0,1,2,3,4)であり、Mが配位数4を有する場合、n=1〜4(1,2,3,4)、m=0〜3(0,1,2,3)及びo=0〜3(0,1,2,3)であり:
さらに、D1は、各々の場合において、互いに独立して、B、C、N、O及びSからなる群より選択される環内ドナー原子であり;
D2は、各々の場合において、互いに独立して、O、S、NR1、N(R1)2、PR1、P(R1)2、P(O)R1、P(O)(R1)2、AsR1、As(R1)2、As(O)R1、As(O)(R1)2、SbR1、Sb(R1)2、Sb(O)R1、Sb(O)(R1)2、BiR1、Bi(R1)2、Bi(O)R1、Bi(O)(R1)2、OR1、SR1、SeR1及びTeR1からなる群より選択される環外ドナー基であり;
X1は、各々の場合において、互いに独立して、C又はNであり;
Cy1は、5〜30の環原子を有する芳香族若しくは芳香族複素環基又は芳香族若しくは芳香族複素環系であって、X1及びD1は、当該芳香族若しくは芳香族複素環基又は当該芳香族若しくは芳香族複素環系中に存在し、D2は、環外ドナー原子又は環外ドナー基として結合している電子デバイス。 - 当該デバイスは、有機エレクトロルミネセンスデバイス(OLED)、有機電界効果トランジスタ(O−FET)、有機薄層トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機集積回路(O−IC)、有機太陽電池(O−SC)、有機電界クエンチデバイス(O−FQD)、発光電気化学セル(LEC)、有機光受容体及び有機レーザーダイオード(O−laser)からなる群より選択されることを特徴とする請求項1に記載の電子デバイス。
- D1は、各々の場合において、互いに独立して、N、O又はSであり、D2は、各々の場合において、互いに独立して、O、S、NR1、N(R1)2、PR1又はP(R1)2である請求項1または2に記載の電子デバイス。
- Yは、NR3である請求項1乃至3のいずれか1項に記載の電子デバイス。
- 当該一般式Iの当該化合物は、配位子Lのみを含んでいるか、当該一般式Iの当該化合物は、六配位であり、2つ若しくは3つの二座配位子L又は2つの三座配位子を含んでいるか、或いは当該一般式Iの当該化合物は、平面四角形又は四面体の様式で配位し、1つ若しくは2つの二座配位子L又は1つの四座配位子Lを含んでいる請求項1乃至6のいずれか1項に記載の電子デバイス。
- 一般式Iの化合物であって、
Yは、各々の場合において、互いに独立して、NR2、O又はSであり;
Xは、各々の場合において、互いに独立して、CR1又はNであり;
R1は、各々の場合において、互いに独立して、H、D、F、Cl、Br、I、CHO、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR2=C(R2)2、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、2〜40のC原子を有する直鎖アルケニル若しくはアルキニル基又は3〜40のC原子を有する分枝若しくは環状アルキル、アルケニル、アルキニル、アルコキシ若しくはチオアルコキシ基であって、それらの各々は、1以上の基R2により置換されていてもよく、1以上の非隣接CH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S又はCONR2により置き換えられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CN又はNO2により置き換えられていてもよいものであるか、5〜60の芳香環原子を有する芳香族又は芳香族複素環系であって、各々の場合において、1以上の基R2により置換されていてもよいものであるか、5〜60の芳香環原子を有するアリールオキシ又はヘテロアリールオキシ基であって、1以上のR2により置換されていてもよいものであるか、或いはこれらの系の組合せであり、2以上の隣接する置換基R1は、単環又は多環の脂肪族若しくは芳香族環系を互いに形成していてもよく;
R2は、各々の場合において、互いに独立して、H、D、F又は1〜20のC原子を有する脂肪族、芳香族及び/又は芳香族複素炭化水素基であって、更に、1以上のH原子はFにより置き換えられていてもよいものであり、2以上の置換基R2は、単環又は多環の脂肪族若しくは芳香族環系を互いに形成していてもよく;
Arは、各々の場合において、互いに独立して、5〜30の芳香環原子を有する芳香族又は芳香族複素環系であって、1以上の非芳香族基R1により置換されていてもよいものであり;
Mが配位数6を有する場合、n=1〜6、o=0〜5及びm=0〜5であり、Mが配位数5を有する場合、n=1〜5、o=0〜4及びm=0〜4であり、Mが配位数4を有する場合、n=1〜4、m=0〜3及びo=0〜3であり、
さらに、D1は、各々の場合において、互いに独立して、B、C、N、O及びSからなる群より選択される環内ドナー原子であり;
D2は、各々の場合において、互いに独立して、O、S、NR1、N(R1)2、PR1、P(R1)2、P(O)R1、P(O)(R1)2、AsR1、As(R1)2、As(O)R1、As(O)(R1)2、SbR1、Sb(R1)2、Sb(O)R1、Sb(O)(R1)2、BiR1、Bi(R1)2、Bi(O)R1、Bi(O)(R1)2、OR1、SR1、SeR1及びTeR1からなる群より選択される環外ドナー基であり;
X1は、各々の場合において、互いに独立して、C又はNであり;
Cy1は、5〜30の環原子を有する芳香族若しくは芳香族複素環基又は芳香族複素環系であって、X1及びD1は、当該芳香族若しくは芳香族複素環基又は当該芳香族若しくは芳香族複素環系中に存在し、D2は、環外ドナー原子又は環外ドナー基として結合している化合物。 - 請求項8乃至10のいずれか1項に記載の当該一般式Iの化合物の、電子デバイスにおける発光化合物、マトリクス材料、正孔ブロッキング材料及び/又は電子輸送材料として
の使用。 - 請求項12に記載の配位子L及び任意の更なる配位子L’、L’’と、式(47)の金属アルコキシド、式(48)の金属ケトケトネート又は式(49)の金属ハロゲン化物との反応による請求項9乃至10のいずれか1項に記載の化合物の製造方法であって、
Halは、同じであるか又は異なり、F、Cl、Br又はIであり;
Ligは、同じであるか又は異なり、中性又はモノアニオン性の単座若しくは二座配位子であり;
qは、同じであるか又は異なり、0、1、2、3又は4、好ましくは、1又は2であり;
rは、同じであるか又は異なり、0、1、2、3、4又は5であり;
ここで、式(48)及び(49)の化合物は、帯電していてもよく、1以上の対イオンを含んでいてもよく;さらに、式(47)乃至(49)、特に式(49)の化合物は、水和物の形態であってもよい製造方法。
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DE102004020298A1 (de) | 2004-04-26 | 2005-11-10 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere und deren Verwendung |
DE102004023277A1 (de) | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Neue Materialmischungen für die Elektrolumineszenz |
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ITRM20040352A1 (it) | 2004-07-15 | 2004-10-15 | Univ Roma La Sapienza | Derivati oligomerici dello spirobifluorene, loro preparazione e loro uso. |
DE102004034517A1 (de) | 2004-07-16 | 2006-02-16 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
EP1669386A1 (de) | 2004-12-06 | 2006-06-14 | Covion Organic Semiconductors GmbH | Teilkonjugierte Polymere, deren Darstellung und Verwendung |
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EP1956022B1 (en) | 2005-12-01 | 2012-07-25 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
DE102006025777A1 (de) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
CN101511834B (zh) | 2006-11-09 | 2013-03-27 | 新日铁化学株式会社 | 有机场致发光元件用化合物及有机场致发光元件 |
DE102007002714A1 (de) | 2007-01-18 | 2008-07-31 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
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-
2009
- 2009-03-02 DE DE102009011223A patent/DE102009011223A1/de not_active Withdrawn
-
2010
- 2010-02-03 DE DE112010000948T patent/DE112010000948A5/de not_active Ceased
- 2010-02-03 KR KR1020117023019A patent/KR101842719B1/ko active IP Right Grant
- 2010-02-03 CN CN201080007829.4A patent/CN102317407B/zh active Active
- 2010-02-03 JP JP2011552336A patent/JP5666483B2/ja active Active
- 2010-02-03 US US13/254,220 patent/US9074128B2/en active Active
- 2010-02-03 WO PCT/EP2010/000635 patent/WO2010099852A1/de active Application Filing
- 2010-02-25 TW TW099105513A patent/TWI568741B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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DE102009011223A1 (de) | 2010-09-23 |
US9074128B2 (en) | 2015-07-07 |
CN102317407A (zh) | 2012-01-11 |
KR20110133583A (ko) | 2011-12-13 |
DE112010000948A5 (de) | 2012-07-19 |
US20120004407A1 (en) | 2012-01-05 |
CN102317407B (zh) | 2014-12-31 |
TWI568741B (zh) | 2017-02-01 |
KR101842719B1 (ko) | 2018-03-27 |
JP2012519384A (ja) | 2012-08-23 |
TW201100439A (en) | 2011-01-01 |
WO2010099852A1 (de) | 2010-09-10 |
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