JP6469673B2 - 電子素子のための材料 - Google Patents
電子素子のための材料 Download PDFInfo
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- JP6469673B2 JP6469673B2 JP2016525945A JP2016525945A JP6469673B2 JP 6469673 B2 JP6469673 B2 JP 6469673B2 JP 2016525945 A JP2016525945 A JP 2016525945A JP 2016525945 A JP2016525945 A JP 2016525945A JP 6469673 B2 JP6469673 B2 JP 6469673B2
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- Prior art keywords
- aromatic ring
- groups
- ring structure
- group
- substituted
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 161
- 150000001875 compounds Chemical class 0.000 claims description 131
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000011159 matrix material Substances 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- HQJPYLIAWVSUHC-UHFFFAOYSA-N ctk1a2241 Chemical group C12=CC=CC=C2C2=CC=CC3=C2C1C1=CC=CC=C31 HQJPYLIAWVSUHC-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 230000005525 hole transport Effects 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000000412 dendrimer Substances 0.000 claims description 17
- 229920000736 dendritic polymer Polymers 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 125000005259 triarylamine group Chemical group 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 230000005684 electric field Effects 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 238000007689 inspection Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 96
- -1 phenanthriimidazole Chemical compound 0.000 description 40
- 125000003545 alkoxy group Chemical group 0.000 description 34
- 125000004001 thioalkyl group Chemical group 0.000 description 30
- 125000003342 alkenyl group Chemical group 0.000 description 25
- 125000000304 alkynyl group Chemical group 0.000 description 25
- 239000002019 doping agent Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 17
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 14
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000004982 aromatic amines Chemical class 0.000 description 8
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 229910052709 silver Inorganic materials 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 230000002950 deficient Effects 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- 238000003747 Grignard reaction Methods 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
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- 239000013074 reference sample Substances 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 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
- 125000002346 iodo group Chemical group I* 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 2
- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical compound C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
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- 239000010703 silicon Substances 0.000 description 1
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- 239000010944 silver (metal) Substances 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 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
- 229910052721 tungsten Inorganic materials 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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Description
Zは、出現毎に同一であるか異なり、CR1またはNであり;
Ar1は、出現毎に同一であるか異なり、1以上のR3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つのAr1基は、単結合またはN(R4)、C(R4)2、OおよびSから選ばれるブリッジにより、互いにブリッジされてもよく;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar1)2、N(R3)2、C(=O)Ar1、C(=O)R3、P(=O)(Ar1)2、P(=O)(R3)2、B(OR3)2、CHO、Si(R3)2、OSO2R3、S(=O)R3、S(=O)2R3、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状アルキル、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(ここで、アルキル、アルコキシ、チオアルキル、アルケニルもしくはアルキニル基は、各場合に、1以上のR3基により置換されてよく、1以上の隣接するもしくは隣接しないCH2基は、-R3C=CR3-、-C≡C-、C=O、C=S、C=Se、C=NR3、-C(=O)NR3-、P(=O)(R3)、-C(=O)O-、Si(R3)2、NR3、-O-、-S-、SOもしくはSO2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。)、または各場合に、1以上のR3基により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造、または、各場合に、1以上のR3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複素環式芳香族環構造であり;ここで、2個以上のR1基は、たがいに結合してよく、および環を形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar1)2、N(R3)2、C(=O)Ar1、C(=O)R3、P(=O)(Ar1)2、P(=O)(R3)2、B(OR3)2、CHO、Si(R3)2、OSO2R3、S(=O)R3、S(=O)2R3、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状アルキル、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(ここで、アルキル、アルコキシ、チオアルキル、アルケニルもしくはアルキニル基は、各場合に、1以上のR3基により置換されてよく、1以上の隣接するもしくは隣接しないCH2基は、-R3C=CR3-、-C≡C-、C=O、C=S、C=Se、C=NR3、-C(=O)NR3-、P(=O)(R3)、-C(=O)O-、Si(R3)2、NR3、-O-、-S-、SOもしくはSO2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。)、または各場合に、1以上のR3基により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造、または、各場合に、1以上のR3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複素環式芳香族環構造であり;
R3は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R4)2、C(=O)Ar1、C(=O)R4、P(=O)(Ar1)2、B(OR4)2、CHO、Si(R4)2、OSO2R4、S(=O)R4、S(=O)2R4、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状アルキル、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(ここで、アルキル、アルコキシ、チオアルキル、アルケニルもしくはアルキニル基は、各場合に、1以上のR4基により置換されてよく、1以上の隣接するもしくは隣接しないCH2基は、-R4C=CR4-、-C≡C-、C=O、C=S、C=Se、C=NR4、-C(=O)NR4-、P(=O)(R4)、-C(=O)O-、Si(R4)2、NR4、-O-、-S-、SOもしくはSO2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。)、または各場合に、1以上のR4基により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造、または、各場合に、1以上のR4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複素環式芳香族環構造であり;ここで、2個以上のR4基は、たがいに結合してよく、および環を形成してよく;
R4は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個の炭素原子を有する脂肪族基、または6〜60個の芳香族環原子を有する芳香族環構造、または5〜60個の芳香族環原子を有する複素環式芳香族環構造であって、ここで、脂肪族基、芳香族環構造もしくは複素環式芳香族環構造中の1以上の水素原子は、D、F、Cl、Br、I、CNもしくは1〜5個の炭素原子を有するアルキル基で置き代えられてよく;ここで、2個以上のR4基は、たがいに結合してよく、および環を形成してよく;
ここで、式(1)中のR2および/または少なくとも一つのR1は、少なくとも一つの芳香族環構造もしくは複素環式芳香族環構造を含み、
少なくとも一つのR1は、少なくとも一つの芳香族環構造もしくは複素環式芳香族環構造を含む場合には、全てのR1とR2中の芳香族環原子の合計数は、少なくとも12個であり;および
R1が、芳香族環構造もしくは複素環式芳香族環構造を含まない場合には、R2は、少なくとも24個の芳香族環原子を含み、12位を介して結合するさらなるインデノ[1,2,3-jk]フルオレン骨格を含まない。
本発明のさらに好ましい1態様では、上記式中のR2は、出現毎に同一であるか異なり、H、D、F、CN、N(Ar1)2、N(R3)2、1〜10個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個の炭素原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜10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(ここで、アルキル、アルコキシ、チオアルキル、アルケニルもしくはアルキニル基は、各場合に、1以上のR3基により置換されてよく、1以上の隣接しないCH2基は、Si(R3)2、-S-もしくは-O-で置き代えられてよく、ここで、1以上の水素原子は、DもしくはFで置き代えられてよい。)、または各場合に、1以上のR3基により置換されてよい6〜30個の芳香族環原子を有する芳香族環構造、または、各場合に、1以上の基R3により置換されてよい5〜30個の芳香族環原子を有する複素環式芳香族環構造である。
Ar2は、出現毎に同一であるか異なり、1以上のR3基により置換されてよい5〜24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、ここで、全てのAr2とAr3中の芳香族環原子の合計数は、共に、60を超えず;
Ar3は、出現毎に同一であるか異なり、複数のR3基の一つにより置換されてよい5〜24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;
Eは、単結合、C(R3)2、NR3、OおよびSから選ばれる。
(A)スズキ重合;
(B)ヤマモト重合;
(C)スチル重合および
(D)ハートウイッグ-ブッフバルト重合
重合をこれらの方法により実行することができる方法と次いでポリマーを反応媒体から分離し、精製することができる方法は、当業者に知られており、文献、たとえば、WO 2003/048225、WO 2004/037887およびWO 2004/037887に詳細に記載されている。
上記記載のエミッターの例は、出願WO 00/70655、WO 01/41512、WO 02/02714、WO 02/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373およびUS2005/0258742に見出すことができる。一般的には、燐光発光OLEDのために先行技術により使用され、有機エレクトロルミネッセンス素子分野の当業者に知られるようなすべての燐光発光錯体が適切である。当業者は発明力を行使することなく、有機エレクトロルミッセンス素子中で式(1)または(2)の化合物と組み合わせてさらなる燐光錯体を使用することもできる。
混合マトリックス系は、一以上のドーパントを含んでよい。本発明によれば、ドーパント化合物は、一緒に、全混合物の0.1〜50.0体積%の割合、好ましくは、全混合物の0.5〜20.0体積%の割合を有する。対応して、マトリックス成分は、一緒に、全混合物の50.0〜99.9体積%、好ましくは、全混合物の80.0〜99.5体積%の割合を有する。
以下の合成を、別段の指定がない限り、保護ガス雰囲気下で実施する。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)。
例6:ビフェニル-4-イル-(9,9-ジメチル-9H-フルオレン-2-イル)-(4-インデノ[1,2,3-jk]フルオレン-7b-イルフェニル)アミン
本発明のOLEDと先行技術のOLEDが、WO 04/058911による一般的方法により製造されるが、ここに記載される状況(層の厚さの変化、材料)に適合される。
青色蛍光参照試料C1を製造し、本発明の試料I1〜I7と比較した。電流密度10mA/cm2における参照試料C1は、外部量子効率6.2%と、寿命(60mA/cm2におけるLD80)120時間とを有する。比較によって、本発明の試料I1(7.5%、160時間)、I2(7.8%、250時間)、I3(7.6%、210時間)、I4(7.4%、200時間)、I5(8.0%、235時間)、I6(7.7%、270時間)、I7(7.1%、260時間)は、10mA/cm2の電流密度でのより良好な量子効率と、より長い寿命(60mA/cm2におけるLD80)との両者を有する。
緑色燐光参照試料C2を製造し、本発明の試料I8〜I12と比較した。電流密度2mA/cm2における参照試料C2は、外部量子効率11.7%と、寿命(20mA/cm2におけるLD80)80時間とを有する。比較によって、本発明の試料I8(17.2%、135時間)、I9(18.7%、110時間)、I10(17.4%、145時間)、I11(19.0%、105時間)、I12(20.2%、160時間)は、2mA/cm2の電流密度でのより良好な量子効率と、より長い寿命(20mA/cm2におけるLD80)との両者を有する。
Claims (12)
- 式(1−3a)〜(1−3g)および(1−5a)〜(1−5g)の化合物;
Ar1は、出現毎に同一であるか異なり、1以上のR3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であり;
Ar2は、出現毎に同一であるか異なり、1以上のR3基により置換されてよい5〜24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、ここで、全てのAr2とAr3中の芳香族環原子の合計数は、共に、60を超えず;
Ar3は、出現毎に同一であるか異なり、複数のR3基の一つにより置換されてよい5〜24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;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar1)2、1〜40個の炭素原子を有する直鎖アルキル基、3〜40個の炭素原子を有する分岐あるいは環状アルキル基、(ここで、アルキル基は、各場合に、1以上のR3基により置換されてよい。)、または各場合に、1以上のR3基により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造、または、各場合に、1以上のR3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複素環式芳香族環構造であり;
R2は、1以上のR3基により置換されてよい6〜30個の芳香族環原子を有する芳香族環構造であり;
R3は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R4)2、1〜40個の炭素原子を有する直鎖アルキル基、3〜40個の炭素原子を有する分岐あるいは環状アルキル基、(ここで、アルキル基は、各場合に、1以上のR4基により置換されてよい。)、または各場合に、1以上のR4基により置換されてよい6〜60個の芳香族環原子を有する芳香族環構造、または、各場合に、1以上のR4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複素環式芳香族環構造であり;
R4は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個の炭素原子を有する脂肪族基、または6〜60個の芳香族環原子を有する芳香族環構造、または5〜60個の芳香族環原子を有する複素環式芳香族環構造であって、ここで、脂肪族基、芳香族環構造もしくは複素環式芳香族環構造中の1以上の水素原子は、D、F、Cl、Br、I、CNもしくは1〜5個の炭素原子を有するアルキル基で置き代えられてよく;
ただし、式(1−3a)において、R1が、芳香族もしくは複素環式芳香族環構造を含まない場合には、基-N(Ar1)2は、少なくとも24個の芳香族環原子を含み、さらなるインデノ[1,2,3-jk]フルオレン骨格を含まず、式(1−3a)において少なくとも一つのR1が、少なくとも一つの芳香族もしくは複素環式芳香族環構造を含む場合には、全てのR1と基-N(Ar1)2中の芳香族環原子の合計数は、少なくとも12個であり、 および
ただし、式(1−5a)において、R1が、芳香族もしくは複素環式芳香族環構造を含まない場合には、基-Ar3-N(Ar2)2は、少なくとも24個の芳香族環原子を含み、さらなるインデノ[1,2,3-jk]フルオレン骨格を含まない。 - インデノ[1,2,3-jk]フルオレン骨格中の5位および10位の少なくとも一つにあるR1は、Hであることを特徴とする、請求項1記載の化合物。
- インデノ[1,2,3-jk]フルオレン骨格中の5位および10位にあるR1は、各場合に存在するのであれば、Cl、Br、I、B(OR3)2、およびCHOを含む基を含まないことを特徴とする、請求項1または2記載の化合物。
- 少なくとも一つのR1は、Hではないことを特徴とする、請求項1〜3何れか1項記載の化合物。
- 少なくとも一つのR1は、芳香族環構造もしくは複素環式芳香族環構造を含むことを特徴とする、請求項1〜4何れか1項記載の化合物。
- 複素環式芳香族環構造としてのR2が、インデノ[1,2,3-jk]フルオレン骨格に直接結合するトリアリールアミン基もしくはトリヘテロアリールアミン基もしくはカルバゾール構造を含む場合には、窒素原子は、インデノ[1,2,3-jk]フルオレン骨格に関して、メタもしくはオルト位に配置されることを特徴とする、請求項1〜5何れか1項記載の化合物。
- 式(1−3a)〜(1−3g)および(1−5a)〜(1−5g)の基本骨格が、一以上のカップリング反応により構築されることを特徴とする、請求項1〜6何れか1項記載の化合物の製造方法。
- オリゴマー、ポリマーもしくはデンドリマーへの結合が、式(1−3a)〜(1−3g)および(1−5a)〜(1−5g)中でR1および/またはR2により置換された任意の所望の位置に位置してよい、請求項1〜6何れか1項記載の一以上の化合物を含む、オリゴマー、ポリマーまたはデンドリマー。
- 請求項1〜6何れか1項記載の少なくとも一つの化合物または請求項8記載の少なくとも一つのポリマー、オリゴマーもしくはデンドリマーと少なくとも一つの溶媒とを含む調合物。
- 請求項1〜6何れか1項記載の少なくとも一つの化合物または請求項8記載の少なくとも一つのポリマー、オリゴマーもしくはデンドリマーを含む電子素子。
- 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)、有機太陽電池(O-SC)、有機光学検査器、有機光受容器、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)、有機レーザーダイオード(O-laser)および有機エレクトロルミネッセンス素子(OLED)から選ばれることを特徴とする、請求項10記載の電子素子。
- 請求項1〜6何れか1項記載の化合物または請求項8記載のポリマー、オリゴマーもしくはデンドリマーが、一以上の以下の機能で使用されることを特徴とする有機エレクトロルミッセンス素子(OLED)から選ばれることを特徴とする、請求項11記載の電子素子:
−正孔輸送もしくは正孔注入層において正孔輸送材料として、
−正孔注入材料として、
−正孔ブロック材料として、
−蛍光発光層のためのエミッターとして、
−発光層においてマトリックス材料として、
−励起子ブロック材料として
−中間層のための材料として。
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