JP6193215B2 - 電子デバイスのための化合物 - Google Patents
電子デバイスのための化合物 Download PDFInfo
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- JP6193215B2 JP6193215B2 JP2014508702A JP2014508702A JP6193215B2 JP 6193215 B2 JP6193215 B2 JP 6193215B2 JP 2014508702 A JP2014508702 A JP 2014508702A JP 2014508702 A JP2014508702 A JP 2014508702A JP 6193215 B2 JP6193215 B2 JP 6193215B2
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- 150000001875 compounds Chemical class 0.000 title claims description 122
- 125000003118 aryl group Chemical group 0.000 claims description 123
- 239000000463 material Substances 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000011159 matrix material Substances 0.000 claims description 42
- 230000005525 hole transport Effects 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000000412 dendrimer Substances 0.000 claims description 18
- 229920000736 dendritic polymer Polymers 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000004001 thioalkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 230000005684 electric field Effects 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
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- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
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- 239000010409 thin film Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims 1
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- 238000006116 polymerization reaction Methods 0.000 description 12
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 9
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
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- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical group C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 description 7
- 150000001716 carbazoles Chemical class 0.000 description 7
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
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- 238000003786 synthesis reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- SZTWOOCCTWBIRQ-UHFFFAOYSA-N 2-chloro-9,9-dimethyl-10-(4-phenylphenyl)acridine Chemical compound C12=CC=C(Cl)C=C2C(C)(C)C2=CC=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1 SZTWOOCCTWBIRQ-UHFFFAOYSA-N 0.000 description 3
- IOEABXFXRWILSK-UHFFFAOYSA-N 2-chloro-9,9-dimethyl-10h-acridine Chemical compound C1=C(Cl)C=C2C(C)(C)C3=CC=CC=C3NC2=C1 IOEABXFXRWILSK-UHFFFAOYSA-N 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
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- 125000004986 diarylamino group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
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- 101100275159 Arabidopsis thaliana COBL7 gene Proteins 0.000 description 2
- 101100180341 Arabidopsis thaliana IWS1 gene Proteins 0.000 description 2
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 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
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- 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
- 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
- 239000004065 semiconductor 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
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material 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
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 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
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 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
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 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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- Y02E10/549—Organic PV cells
Description
Ar*は、出現するごとに同一であるかまたは異なり、6〜24個の芳香族環原子を有する芳香族環系または5〜18個の芳香族環原子を有する電子リッチなヘテロアリール基(これらの各々は、1以上のラジカルR2により置換されていてもよい)であり;
Lは、出現するごとに同一であるかまたは異なり、単結合、C=O、C=NR2、Si(R2)2、PR2、P(=O)(R2)、O、S、SO、SO2、1〜20個のC原子を有するアルキレン基、または2〜20個のC原子を有するアルケニレンもしくはアルキニレン基(ここで、前述の基における1以上のCH2基は、C=O、C=NR2、C=O−O、C=O−NR2、Si(R2)2、NR2、P(=O)(R2)、O、S、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または6〜24個の芳香族環原子を有する芳香族環系(これは、1以上のラジカルR2により置換されていてもよい)、または前述の基から選択される1、2、3、4または5個の同一または異なる基の任意の所望の組合せであり;
Xは、C(R1)2、Si(R1)2、NR1、PR1、OおよびSから選択される二価の基であり;
Zは、出現するごとに同一であるかまたは異なり、Zが置換基を有していなければCR2またはNであり、Zが置換基を有していればCであり;
R1は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルキル基、または3〜20個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルキル基、または2〜20個のC原子を有するアルケニルもしくはアルキニル基(ここで、前述の基は、それぞれ1以上のラジカルR3により置換されていてもよく、前述の基における1以上のCH2基は、−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=S、C=NR3、−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または6〜30個の芳香族環原子を有する芳香族環系(これは、各々の場合、1以上のラジカルR3により置換されていてもよい)であり、ここで2以上の非芳香族ラジカルR1は、互いに連結され環を形成していてもよく;
R2は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルキル基、または3〜20個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルキル基、または2〜20個のC原子を有するアルケニルもしくはアルキニル基(ここで、前述の基は、それぞれ1以上のラジカルR3により置換されていてもよく、前述の基における1以上のCH2基は、−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=S、C=NR3、−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これは、各々の場合、1以上のラジカルR3により置換されていてもよい)、または5〜30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(これは、1以上のラジカルR3により置換されていてもよい)であり、ここで2以上のラジカルR2は、互いに連結され環を形成していてもよく;
R3は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、C(=O)R4、CN、Si(R4)3、NO2、P(=O)(R4)2、S(=O)R4、S(=O)2R4、1〜20個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルキル基、または3〜20個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルキル基、または2〜20個のC原子を有するアルケニルもしくはアルキニル基(ここで、前述の基は、それぞれ1以上のラジカルR4により置換されていてもよく、前述の基における1以上のCH2基は、−R4C=CR4−、−C≡C−、Si(R4)2、C=O、C=S、C=NR4、−C(=O)O−、−C(=O)NR4−、NR4、P(=O)(R4)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これは、各々の場合、1以上のラジカルR4により置換されていてもよい)、または5〜30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(これは、1以上のラジカルR4により置換されていてもよい)であり、ここで2以上のラジカルR3は、互いに連結され環を形成していてもよく;
R4は、出現するごとに同一であるかまたは異なり、H、D、F、または1〜20個のC原子を有する脂肪族、芳香族もしくはヘテロ芳香族有機ラジカル(ここで更に、1以上のH原子は、DまたはFにより置きかえられていてもよい)であり;ここで2以上の置換基R4は、互いに連結され環を形成していてもよく;
nは、出現するごとに同一であるかまたは異なり、0または1であり、ここで少なくとも2つの指数nは、1でなければならず;n=0の場合、基R2は、対応する位置で結合し;
ここで、当該化合物は、カルバゾール基を含有せず;
ここで、5〜18個の芳香族環原子を有する電子リッチなヘテロアリール基または12〜24個の芳香族環原子を有する芳香族環系を表す少なくとも1つの基Ar*は、当該化合物に存在しなければならない。
Yは、NR2、PR2、OおよびSから選択され;
pは、出現するごとに0または1であり、ここでp=0の場合、ラジカルR2は、関連する位置で結合し、Y=NR2の場合、2つの指数pは、両方とも1であることはなく;
当該基は、すべてのフリーの位置でラジカルR2により置換され、
当該基は、基Lに任意の所望の位置で連結されていてもよく、ここで、当該結合は、結合NR2またはPR2の位置で起こっていてもよい。
当該基は、基Lに任意の所望の位置で連結されていてもよく、ここで、当該結合は、結合NR2の位置で起こってもよい。
出現する種々の基L−Ar*は、ここでは次の通りに表示される(式(I−A−2)の例について示す:
(A)SUZUKI重合;
(B)YAMAMOTO重合;
(C)STILLE重合;および
(D)HARTWIG−BUCHWALD重合。
1.本発明による化合物は、特にそれらの高い正孔移動度により、有機エレクトロルミネセンスデバイスの正孔輸送層または正孔注入層において使用するために非常に高度に好適である。
30.3g(116mmol)の2−[2−(4−クロロフェニルアミノ)フェニル]プロパン−2−オールを700mlの脱気トルエンに溶解し、93gのポリリン酸および61.7gのメタンスルホン酸の懸濁液を添加し、混合物を室温で1時間撹拌し、50℃で1時間加熱した。バッチを冷却し、氷に添加し、酢酸エチルで3回抽出した。合わせた有機相を飽和塩化ナトリウム溶液で洗浄し、硫酸マグネシウムで乾燥させ、蒸発させた。ヘプタン/酢酸エチル(20:1)を用いるシリカゲルに通す粗生成物の濾過により、25.1g(89%)の2−クロロ−9,9−ジメチル−9,10−ジヒドロアクリジンを淡黄色結晶として得た。
OLEDの製造
本発明によるOLEDおよび先行技術に従うOLEDは、WO04/058911に従う一般的プロセスにより製造され、これは、本明細書において記述されている状況(層厚さの変動、材料)に適合される。
本発明による化合物は、特に、OLEDにおけるHTM(正孔輸送材料)またはEBM(電子ブロッキング材料)として好適である。これらは、単層において使用するためだけでなく、HTM、EBMとしての混合構成要素として、または発光層の構成成分としても好適である。先行技術に従う比較デバイス(V1〜V8)と比較して、本発明による化合物を含むすべての試料は、より高い効率を同じまたは改善された寿命と一緒に呈する(E1〜E6)。
Claims (13)
- 式(I)の化合物
Ar*は、出現するごとに同一であるかまたは異なり、下記の式(H)であり;
Yは、OおよびSから選択され;
pは1であり;
式(H)の基は、すべてのフリーの位置で基R2により置換され、
式(H)の基は、基Lに任意の所望の位置で連結されていてもよく;
または、
基Ar*は、6〜24個の芳香族環原子を含有する芳香族環系を表し、これは、1以上の基R2により置換されていてもよい;
Lは、出現するごとに同一であるかまたは異なり、単結合、または6〜24個の芳香族環原子を有する芳香族環系(これは、1以上の基R2により置換されていてもよい)であり;
Xは、C(R1)2、Si(R1)2、NR1 およびPR1 から選択される二価の基であり;
Zは、出現するごとに同一であるかまたは異なり、Zが置換基を有していなければCR2またはNであり、Zが置換基を有していればCであり;
R1は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルキル基、または3〜20個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルキル基、または2〜20個のC原子を有するアルケニルもしくはアルキニル基(ここで、前述の基は、それぞれ1以上の基R3により置換されていてもよく、前述の基における1以上のCH2基は、−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=S、C=NR3、−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または6〜30個の芳香族環原子を有する芳香族環系(これは、各々の場合、1以上の基R3により置換されていてもよい)であり、ここで2以上の非芳香族基R1は、互いに連結され環を形成していてもよく;
R2は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルキル基、または3〜20個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルキル基、または2〜20個のC原子を有するアルケニルもしくはアルキニル基(ここで、前述の基は、それぞれ1以上の基R3により置換されていてもよく、前述の基における1以上のCH2基は、−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=S、C=NR3、−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これは、各々の場合、1以上の基R3により置換されていてもよい)、または5〜30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(これは、1以上の基R3により置換されていてもよい)であり、ここで2以上の基R2は、互いに連結され環を形成していてもよく;
R3は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、C(=O)R4、CN、Si(R4)3、NO2、P(=O)(R4)2、S(=O)R4、S(=O)2R4、1〜20個のC原子を有する直鎖のアルキル、アルコキシもしくはチオアルキル基、または3〜20個のC原子を有する分枝もしくは環状のアルキル、アルコキシもしくはチオアルキル基、または2〜20個のC原子を有するアルケニルもしくはアルキニル基(ここで、前述の基は、それぞれ1以上の基R4により置換されていてもよく、前述の基における1以上のCH2基は、−R4C=CR4−、−C≡C−、Si(R4)2、C=O、C=S、C=NR4、−C(=O)O−、−C(=O)NR4−、NR4、P(=O)(R4)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、前述の基における1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5〜30個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これは、各々の場合、1以上の基R4により置換されていてもよい)、または5〜30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(これは、1以上の基R4により置換されていてもよい)であり、ここで2以上の基R3は、互いに連結され環を形成していてもよく;
R4は、出現するごとに同一であるかまたは異なり、H、D、F、または1〜20個のC原子を有する脂肪族、芳香族もしくはヘテロ芳香族有機基(ここで更に、1以上のH原子は、DまたはFにより置きかえられていてもよい)であり;ここで2以上の置換基R4は、互いに連結され環を形成していてもよく;
nは、出現するごとに同一であるかまたは異なり、0または1であり、ここで少なくとも2つの指数nは、1でなければならず;n=0の場合、基R2は、対応する位置で結合し;
ここで、当該化合物は、カルバゾール基を含有せず;
ここで、式(H)である少なくとも1つの基Ar*は、当該化合物に存在しなければならない。 - 基Lは、単結合であることを特徴とする請求項1に記載の化合物。
- 正確に1個の基L−Ar*は、式(I)の基本構造の窒素原子に結合し、正確に1個の更なる基L−Ar*は、式(I)の基本構造の芳香族6員環に結合することを特徴とする請求項1または2に記載の化合物。
- 式(I)の基本構造の芳香族6員環に対する基L−Ar*の結合位置は、窒素原子に対してパラ位またはメタ位であることを特徴とする請求項1〜3の何れか1項に記載の化合物。
- Xは、C(R1)2 であることを特徴とする請求項1〜4の何れか1項に記載の化合物。
- 式(I)の基本構造の芳香族6員環につき最大1個の基Zが、Nであることを特徴とする請求項1〜5の何れか1項に記載の化合物。
- Xが基C(R1)2を表す場合、基C(R1)2の基R1は、芳香族環系を表さず、かつ、アリール基を表さないことを特徴とする請求項1〜6の何れか1項に記載の化合物。
- ケト基、リンオキサイド基、硫黄オキサイド基を含有しないことを特徴とする請求項1〜7の何れか1項に記載の化合物。
- 請求項1〜8の何れか1項に記載の1以上の化合物を含有するオリゴマー、ポリマーもしくはデンドリマーであって、前記ポリマー、オリゴマーもしくはデンドリマーに対する結合が、R1またはR2により置換されている式(I)の任意の所望の位置に位置していてもよい、オリゴマー、ポリマーもしくはデンドリマー。
- 請求項1〜8の何れか1項に記載の少なくとも1の化合物または請求項9に記載の少なくとも1のポリマー、オリゴマーもしくはデンドリマー、および少なくとも1の溶媒を含む配合物。
- 請求項1〜8の何れか1項に記載の少なくとも1の化合物または請求項9に記載の少なくとも1のポリマー、オリゴマーもしくはデンドリマーを含む電子デバイス。
- 有機集積回路(O−IC)、有機電界効果トランジスタ(O−FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機ソーラーセル(O−SC)、有機光学検出器、有機感光体、有機電場消光デバイス(O−FQD)、発光電気化学セル(LEC)または有機レーザーダイオード(O−レーザー)および有機エレクトロルミネセンスデバイス(OLED)から選択されることを特徴とする請求項11に記載の電子デバイス。
- 請求項1〜8の何れか1項に記載の少なくとも1の化合物または請求項9に記載の少なくとも1のポリマー、オリゴマーもしくはデンドリマーが、以下の機能の1つ以上において使用されることを特徴とする、有機エレクトロルミネセンスデバイスの群から選択される請求項11に記載の電子デバイス:
− 正孔輸送層もしくは正孔注入層における正孔輸送材料としての機能、
− 発光層におけるマトリクス材料としての機能、
− 電子ブロッキング材料としての機能、
− 励起子ブロッキング材料としての機能。
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KR20210002044A (ko) | 2019-06-27 | 2021-01-06 | 간또 가가꾸 가부시끼가이샤 | 스피로 아크리단 기반 화합물, 이를 포함하는 정공 수송 재료, 및 정공 수송층에 이를 포함하는 유기 전자 디바이스 |
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