JP6416244B2 - 有機エレクトロルミネッセンス素子のためのスピロ縮合ラクタム化合物 - Google Patents
有機エレクトロルミネッセンス素子のためのスピロ縮合ラクタム化合物 Download PDFInfo
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- JP6416244B2 JP6416244B2 JP2016522301A JP2016522301A JP6416244B2 JP 6416244 B2 JP6416244 B2 JP 6416244B2 JP 2016522301 A JP2016522301 A JP 2016522301A JP 2016522301 A JP2016522301 A JP 2016522301A JP 6416244 B2 JP6416244 B2 JP 6416244B2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- KNVVMNKJHCIPRV-UHFFFAOYSA-M lithium;3-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=CC=C2N=C(C([O-])=O)C(O)=CC2=C1 KNVVMNKJHCIPRV-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 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
- AACVIJSESUHQOI-UHFFFAOYSA-N n-phenylthiophen-3-amine Chemical compound C=1C=CC=CC=1NC=1C=CSC=1 AACVIJSESUHQOI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 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
- 238000007645 offset printing Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 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
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 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
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 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
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
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- 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
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- C07D471/12—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 three hetero rings
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- C07D471/22—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 systems contains four or more hetero rings
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Description
Xは、出現毎に同一であるか異なり、CRもしくはNであるか、または環中の丁度2個の隣接するX基は、NR、OおよびSから選ばれ、一緒に5員環を形成し;
Yは、Ar1が、6員アリールもしくはヘテロアリール基の場合は、Cであるか、またはAr1が、5員ヘテロアリール基の場合は、CもしくはNであり;
Eは、NR、CR2、O、S、C=O、SiR2、SOまたはSO2であり;
Ar1は、Y基と明示された炭素原子と一緒になって、1以上のR基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Ar2、Ar3は、出現毎に同一であるか異なり、明示された炭素原子と一緒になって、1以上のR基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R1)2、C(=O)Ar4、C(=O)R1、P(=O)(Ar4)2、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルキル基、2〜40個の炭素原子を有するアルケニルもしくはアルキニル基(夫々、1以上のR1基により置換されてよく、1以上の隣接しないCH2基は、R1C=CR1、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SもしくはCONR1で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、各場合に、1以上のR1基により置換されてよい5〜80個の、好ましくは、5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR1基により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、これらの構造の組み合わせから選ばれ;ここで、2個以上の隣接するR置換基は、1以上のR1基により置換されてよい単環式あるいは多環式の脂肪族、芳香族もしくは複素環式芳香族環構造を形成することが随意に可能であり;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R2)2、C(=O)Ar4、C(=O)R2、P(=O)(Ar4)2、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルキル基、2〜40個の炭素原子を有するアルケニルもしくはアルキニル基(夫々、1以上のR2基により置換されてよく、1以上の隣接しない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もしくはCONR2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、各場合に、1以上のR2基により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR2基により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、これらの構造の組み合わせから選ばれ;ここで、2個以上の隣接するR置換基は、1以上のR2基により置換されてよい単環式あるいは多環式の脂肪族、芳香族もしくは複素環式芳香族環構造を形成することが随意に可能であり;
Ar4は、出現毎に同一であるか異なり、1以上の非芳香族R2基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;同時に、同じ窒素原子もしくは燐原子に結合する2個のAr4基は、単結合または、N(R2)、C(R2)およびOから選ばれるブリッジにより互いにブリッジされてよく、
R2は、H、D、F、CN、1〜20個の炭素原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上の水素原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよく、ここで、2個以上の隣接するR2置換基は、一緒になって、単環式あるいは多環式の脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよい。
Wは、出現毎に同一であるか異なり、CRもしくはNであるか、または二個の隣接するW基は、次の式(7)もしくは(8)の基であり、
Vは、NR、OまたはSである。
Xは、出現毎に同一であるか異なり、CRもしくはNであり、ここで、環毎の1個を超えないXは、Nであり;
Eは、出現毎に同一であるか異なり、NRであり、ここでRは、HもしくはDではなく、CR2、O、SもしくはC=Oであり;
Ar1は、上記言及した式(2)、(3)、(4)、(5)および(6)の基から選ばれ;
Ar2は、上記言及した式(9)、(10)および(11)の基から選ばれ;
Ar3は、上記言及した式(12)、(13)、(14)および(15)の基から選ばれる。
Xは、出現毎に同一であるか異なり、CRであり;
Eは、出現毎に同一であるか異なり、NRであり、ここでRは、HもしくはDではなく、CR2もしくはOであり;
Ar1は、上記言及した式(2)、(3)、(4)、(5)および(6)の基から選ばれ;
Ar2は、上記言及した式(9)、(10)および(11)の基から選ばれ;、
Ar3は、上記言及した式(12)、(13)、(14)および(15)の基から選ばれる。
使用されるさらなる記号は、上記の定義を有する。
a)アクリジン、キサントン、チオキサンテノンまたはアントラセン-9-オン誘導体に由来するスピロ化合物を調製すること、および
b)窒素を置換し、次いで、環化によりラクタムを得ること。
以下の合成は、他に断らない限り、保護ガス雰囲気下で行われる。反応物は、ALDRICHまたはABCRから市販されている(酢酸パラジウム(II)、トリ-o-トリルホスフィン、無機材料、溶媒)。フェニルアクリドンと、10-[1,1’-ジフェニル]-4-イルアクリジノンと、さらなる誘導体との合成を、文献(Chemical Communications, 48(86), 10678-10680; 2012)にしたがって行うことができ、文献から知られている。角括弧内の数字は文献から知られている化合物のCAS番号である。
a)tert-ブチル(2-ブロモフェニル)フェニルカルバメートの合成
例2からの93g(158ミリモル)の化合物を、保護雰囲気下で500mLのジメチルホルムアミド中に溶解させる。この溶液に対し、17.3g(0.075モル)のベンジルトリメチルアンモニウムブロミドと、31.28g(0.226モル)の炭酸カリウムを添加する。その後、保護ガス下で、5.08g(0.022モル)のPd(OAc)2を添加し、その混合物を120℃で9時間撹拌する。この時間後、反応混合物を室温に冷まし、ジクロロメタンで抽出する。結合した有機相を、Na2SO4で脱水させ、濃縮する。残留物をn−ヘプタンから再結晶化させる。収率:64g(126ミリモル)、80%。
以下の例C1〜I14(表1と2参照)では、種々のOLEDのデータが提示されている。厚さ50nmの構造化されたITO(インジウム錫酸化物)で被覆された、清浄にした(研究室の食器洗浄機、Merck Extran洗浄剤で洗浄した)ガラス薄板が、改善された加工のために、20nmのPEDOT:PSS(ポリ(3,4-エチレンジオキシチオフェン)ポリ(スチレンスホネート)で水性溶液からのスピン、(Heraeus Precious Metals GmbH 独からCLEVIOS(登録商標) P VP AI 4083として購入)で被覆される。これらの被覆されたガラス薄板はOLEDが適用される基板を形成する。OLEDは、基本的に、次の層構造を有する:基板/正孔輸送層(HTL)/中間層(IL)/電子ブロック層(EBL)/発光層(EML)/随意に、正孔ブロック層(HBL)/電子輸送層(ETL)/随意に、電子注入層(EIL)および最後にカソード。カソードは、100nm厚のアルミニウム層により形成される。OLEDの正確な構造を、表1に見ることができる。OLEDの製造のために必要とされる材料は、表3に示されている。ここでは、「4a」などのラベルは、例4aで合成された材料に関する。同じことが他の本発明の材料にも適用される。
ラクタムのスピロ基中の5員環(先行技術)を、6員環(本発明)に交換することによって、約40%のパワー効率の改善が、マトリックス材料として使用する場合に得られる(例C1、I2)。さらに、本発明の化合物は駆動寿命において著しい改善を与える。20mA/cm2での駆動における、マトリックス材料として化合物PA1を含むOLEDの場合の初期輝度は、90時間(例C1)または115時間(例C2)後に、80%に低下するが、このことは、160時間(例I1)後まで、化合物4sを含む対応するOLEDには当てはまらず、換言すると、寿命では40%を超える増加が得られる。化合物4iについては、初期輝度は120時間(例I2)後、80%に低下する。
Claims (10)
- 式(16)〜(25)の化合物、
Xは、出現毎に同一であるか異なり、CRもしくはNであり;
Eは、NR、CR2、O、S、C=O、SiR2、SOまたはSO2であり;
Vは、NR、OまたはSであり;
Wは、出現毎に同一であるか異なり、CRもしくはNであり;
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R1)2、C(=O)Ar4、C(=O)R1、P(=O)(Ar4)2、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基、2〜40個の炭素原子を有するアルケニルもしくはアルキニル基(夫々、1以上のR1基により置換されてよく、1以上の隣接しないCH2基は、R1C=CR1、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SもしくはCONR1で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、1以上のR1基により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR1基により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、これらの構造の組み合わせから選ばれ;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R2)2、C(=O)Ar4、C(=O)R2、P(=O)(Ar4)2、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基、2〜40個の炭素原子を有するアルケニルもしくはアルキニル基(夫々、1以上のR2基により置換されてよく、1以上の隣接しない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もしくはCONR2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、1以上のR2基により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR2基により置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または、これらの構造の組み合わせから選ばれ;
Ar4は、出現毎に同一であるか異なり、1以上の非芳香族R2基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
R2は、H、D、F、CN、1〜20個の炭素原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上の水素原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよい。 - 式(16a)〜(25a)の化合物から選ばれる、請求項1記載の化合物。
- 式(16b)〜(25b)の化合物から選ばれる、請求項1または2記載の化合物。
- EはNRであり、Rは1以上のR1基により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造から選ばれることを特徴とする、請求項1〜3何れか1項記載の化合物。
- EはNRであり、Rは、1以上のR 1 基により置換されてよいフェニル、オルト-、メタ-もしくはパラ-ビフェニル、オルト-、メタ-、パラ-もしくは分岐テルフェニル、オルト-、メタ-、パラ-もしくは分岐クアテルフェニル、1-,2-,3-もしくは4-フルオレニル、1-,2-,3-もしくは4-スピロビフルオレニル、トリアジン、1-,2-,3-もしくは4-ジベンゾフラニル、1-,2-,3-もしくは4-ジベンゾチエニル、1-,2-,3-もしくは4-カルバゾリルから選ばれることを特徴とする、請求項1〜4何れか1項記載の化合物。
- 請求項1〜5何れか1項記載の少なくとも一つの化合物と少なくとも一つの溶媒を含む調合物。
- 請求項1〜5何れか1項記載の一以上の化合物を含み、ポリマー、オリゴマーもしくはデンドリマーの一以上の結合が存在する、オリゴマー、ポリマーもしくはデンドリマー。
- 請求項1〜5何れか1項記載の化合物または請求項7記載のオリゴマー、ポリマーもしくはデンドリマーの、電子素子での使用。
- 請求項1〜5何れか1項記載の一以上の化合物または請求項7記載のオリゴマー、ポリマーもしくはデンドリマーを含む、有機エレクトロルミネッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、有機染料増感性太陽電池、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学電池、有機レーザーダイオードおよび有機プラスモン発光素子より成る群から選ばれる、電子素子。
- 有機エレクトロルミッセンス素子であって、請求項1〜5何れか1項記載の化合物が、蛍光もしくは燐光エミッターのためのマトリックス材料として、および/または正孔ブロック層中で、および/または電子輸送層中で、および/または電子ブロックもしくは励起子ブロック層中で、および/または正孔輸送層中で使用されることを特徴とする、請求項9記載の電子素子。
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US11121327B2 (en) | 2021-09-14 |
EP3016952A1 (de) | 2016-05-11 |
JP2016523869A (ja) | 2016-08-12 |
WO2015000542A1 (de) | 2015-01-08 |
CN105593228A (zh) | 2016-05-18 |
CN105593228B (zh) | 2018-11-02 |
US20160372681A1 (en) | 2016-12-22 |
EP3016952B1 (de) | 2019-05-15 |
KR20160027155A (ko) | 2016-03-09 |
KR102238852B1 (ko) | 2021-04-09 |
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