JP2012518285A - 有機電子デバイス - Google Patents
有機電子デバイス Download PDFInfo
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- JP2012518285A JP2012518285A JP2011550439A JP2011550439A JP2012518285A JP 2012518285 A JP2012518285 A JP 2012518285A JP 2011550439 A JP2011550439 A JP 2011550439A JP 2011550439 A JP2011550439 A JP 2011550439A JP 2012518285 A JP2012518285 A JP 2012518285A
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- -1 aromatic nitrogen heterocyclic compound Chemical class 0.000 claims abstract description 46
- 238000002347 injection Methods 0.000 claims abstract description 36
- 239000007924 injection Substances 0.000 claims abstract description 36
- 230000000903 blocking effect Effects 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 239000000463 material Substances 0.000 claims description 73
- 230000005525 hole transport Effects 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000000412 dendrimer Substances 0.000 claims description 12
- 229920000736 dendritic polymer Polymers 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 230000002950 deficient Effects 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 238000007740 vapor deposition Methods 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 238000000859 sublimation Methods 0.000 claims description 3
- 230000008022 sublimation Effects 0.000 claims description 3
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims description 2
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012159 carrier gas Substances 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 238000005092 sublimation method Methods 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 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 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 125000005259 triarylamine group Chemical group 0.000 description 10
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 8
- 150000004982 aromatic amines Chemical class 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- MGHIAZXMZPFDDA-UHFFFAOYSA-N 2,3,4-trichloro-2,3,4,6,7,8,10-heptazatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaene Chemical compound ClN1N(N(C=2C=CN=C3N=NN=C1C23)Cl)Cl MGHIAZXMZPFDDA-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 101100042788 Caenorhabditis elegans him-1 gene Proteins 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 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 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- UUMYLIPVZOJGBE-UHFFFAOYSA-N 2,3,4-triphenyl-2,3,4,6,7,8,10-heptazatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaene Chemical compound C1(=CC=CC=C1)N1N(N(C=2C=CN=C3N=NN=C1C23)C2=CC=CC=C2)C2=CC=CC=C2 UUMYLIPVZOJGBE-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
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- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 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
- 125000001828 phenalenyl group Chemical class C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 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
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-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
- 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
- 230000009103 reabsorption Effects 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
【選択図】 なし
Description
Xは各々の出現において、同一または異なっており、CR1またはNであり;
Yは各々の出現において、同一または異なっており、B(R1)2、C(R1)2、NR1、O、S、C(=O)、C=C(R1)2、S(=O)、S(=O)2、P(=O)(R1)2からなる群より選択される2価の基、または1以上の基R1によって置換されていてもよい、5ないし18の芳香環原子を有する2価の芳香環系または複素芳香環系であり;
Rは各々の出現において、同一または異なっており、H、D、F、Cl、Br、I、CHO、N(R1)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR1=CR1Ar、CN、NO2、Si(R1)3、B(OR1)2、B(R1)2、B(Ar)2、B(N(R1)2)2、OSO2R1、1ないし40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コキシ基または2ないし40のC原子を有する直鎖のアルケニルもしくはアルキニル基または3ないし40のC原子を有する分枝もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1以上の基R1で置換されていてもよく、ここで1以上の非隣接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またはCONR1で置換されていてもよく、ここで1以上のH原子はD、F、Cl、Br、I、CNまたはNO2で置換されていてもよい、または5ないし60の芳香環原子を有する芳香環系もしくは複素芳香環系であり、これらは各々の場合に1以上の基R1で置換されていてもよい、または5ないし60の芳香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であり、これらは各々の場合に1以上の基R1で置換されていてもよい、またはこれらの系の組み合わせであり;
R1は各々の出現において、同一または異なっており、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=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1ないし40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コキシ基または2ないし40のC原子を有する直鎖のアルケニルもしくはアルキニル基または3ないし40のC原子を有する分枝もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1以上の基R2で置換されていてもよく、ここで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またはCONR2で置換されていてもよく、ここで1以上のH原子はD、F、Cl、Br、I、CNまたはNO2で置換されていてもよい、または5ないし60の芳香環原子を有する芳香環系もしくは複素芳香環系であり、これらは各々の場合に1以上の基R2で置換されていてもよい、または5ないし60の芳香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であり、これらは1以上の基R2で置換されていてもよい、またはこれらの系の組み合わせであり;
Arは各々の出現において、同一または異なっており、5ないし30の芳香環原子を有する芳香環系または複素芳香環系であり、これらは1以上の非芳香族基R1で置換されていてもよく;ここで同一の窒素またはリン原子に結合した2つの基Arは、単結合またはB(R2)、C(R2)2、Si(R2)2、C=O、C=NR2、C=C(R2)2、O、S、S=O、SO2、N(R2)、P(R2)およびP(=O)R2から選択されるブリッジによって互いに連結していてもよく;
R2は各々の出現において、同一または異なっており、H、Dまたは1ないし20のC原子を有する脂肪族、芳香族および/または複素芳香族炭化水素基であり、さらにH原子はFで置換されていてもよく;ここで2以上の隣接置換基R2は互いに単環または多環の脂肪族または芳香環系を形成してもよく;
nは0、1、2、3、4、5または6であり;
mは0、1、2または3であり;
pは各々の出現において、同一または異なっており、0、1、2または3であり、ここでp=0はユニットの間に単結合があることを意味する。
1.前記式(1)ないし(6)の化合物は高い熱安定性を有し、分解なしに消化できる。
以下の合成は、特に指示がない限り、保護ガス雰囲気下、乾燥溶媒中で行った。溶媒および試薬はALDRICHまたはABCRから購入できる。前駆体トリクロロヘプタアザフェナレンはEP 1854797に従って調製できる。トリクロロヘプタアザフェナレンおよびトリメシチルヘプタアザフェナレンは H. Schroeder et al., J. Org. Chem. 1962, 27, 4262-4266の方法によって調製できる。
本発明によるOLEDを一般的な方法(WO 04/058911に従う)によって製造するが、本明細書に記載した状況に適合させている(層厚変化、使用材料)。
Claims (15)
- カソードと、アノードと、カソードとアノードとの間に配置され式(1)または式(2)の少なくとも1つの化合物を含む少なくとも1つの有機層とを有する有機電子デバイスであって、
Xは各々の出現において、同一または異なっており、CR1またはNであり;
Yは各々の出現において、同一または異なっており、B(R1)2、C(R1)2、NR1、O、S、C(=O)、C=C(R1)2、S(=O)、S(=O)2、P(=O)(R1)2からなる群より選択される2価の基、または1以上の基R1によって置換されていてもよい、5ないし18の芳香環原子を有する2価の芳香環系または複素芳香環系であり;
Rは各々の出現において、同一または異なっており、H、D、F、Cl、Br、I、CHO、N(R1)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR1=CR1Ar、CN、NO2、Si(R1)3、B(OR1)2、B(R1)2、B(Ar)2、B(N(R1)2)2、OSO2R1、1ないし40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コキシ基または2ないし40のC原子を有する直鎖のアルケニルもしくはアルキニル基または3ないし40のC原子を有する分枝もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1以上の基R1で置換されていてもよく、ここで1以上の非隣接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またはCONR1で置換されていてもよく、ここで1以上のH原子はD、F、Cl、Br、I、CNまたはNO2で置換されていてもよい、または5ないし60の芳香環原子を有する芳香環系もしくは複素芳香環系であり、これらは各々の場合に1以上の基R1で置換されていてもよい、または5ないし60の芳香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であり、これらは各々の場合に1以上の基R1で置換されていてもよい、またはこれらの系の組み合わせであり;
R1は各々の出現において、同一または異なっており、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=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1ないし40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コキシ基または2ないし40のC原子を有する直鎖のアルケニルもしくはアルキニル基または3ないし40のC原子を有する分枝もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1以上の基R2で置換されていてもよく、ここで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またはCONR2で置換されていてもよく、ここで1以上のH原子はD、F、Cl、Br、I、CNまたはNO2で置換されていてもよい、または5ないし60の芳香環原子を有する芳香環系もしくは複素芳香環系であり、これらは各々の場合に1以上の基R2で置換されていてもよい、または5ないし60の芳香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であり、これらは1以上の基R2で置換されていてもよい、またはこれらの系の組み合わせであり;
Arは各々の出現において、同一または異なっており、5ないし30の芳香環原子を有する芳香環系または複素芳香環系であり、これらは1以上の非芳香族基R1で置換されていてもよく;ここで同一の窒素またはリン原子に結合した2つの基Arは、単結合またはB(R2)、C(R2)2、Si(R2)2、C=O、C=NR2、C=C(R2)2、O、S、S=O、SO2、N(R2)、P(R2)およびP(=O)R2から選択されるブリッジによって互いに連結していてもよく;
R2は各々の出現において、同一または異なっており、H、Dまたは1ないし20のC原子を有する脂肪族、芳香族および/または複素芳香族炭化水素基であり、さらにH原子はFで置換されていてもよく;ここで2以上の隣接置換基R2は互いに単環または多環の脂肪族または芳香環系を形成してもよく;
nは0、1、2、3、4、5または6であり;
mは0、1、2または3であり;
pは各々の出現において、同一または異なっており、0、1、2または3である、
有機電子デバイス。 - 請求項1による有機電子デバイスであって、有機エレクトロルミネセンスデバイス(OLED)、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)、有機光ディテクタ、有機光レセプター、有機電界消光デバイス(O−FQD)、発光電気化学セル(LEC)およ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、有機電子デバイス。
- 請求項1ないし3のいずれか1項による有機電子デバイスであって、前記式(1)、(3)および(4)の化合物における添字nは0、1または2、特に好ましくは0または1、極めて特に好ましくは0を表し、前記式(2)、(5)および(6)の化合物における添字mは0、1または2、特に好ましくは1を表す、ことを特徴とする有機電子デバイス。
- 請求項1ないし4のいずれか1項による有機電子デバイスであって、前記式(1)ないし(6)の化合物中のRは、各々の出現において同一または異なっており、F、N(R1)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、CN、NO2、1ないし10のC原子を有する直鎖のアルキル基または3ないし40のC原子を有する分枝もしくは環式のアルキル基を表し、これらの各々は1以上の基R1で置換されていてもよく、ここで1以上のH原子はFまたはCNで置換されていてもよい、または5ないし40の芳香環原子を有する芳香環系もしくは複素芳香環系を表し、これらは各々の場合に1以上の基R1で置換されていてもよい、ことを特徴とする有機電子デバイス。
- 請求項5による有機電子デバイスであって、前記式(1)ないし(6)の化合物中のRは、各々の出現において同一または異なっており、F、CN、CF3または5ないし30の芳香環原子を有する芳香環系もしくは複素芳香環系を表し、これらは各々の場合に1以上の基R1で置換されていてもよく、ここで好ましい芳香環系もしくは複素芳香環系はフェニル、2−、3−もしくは4−ピリジル、ピラジニル、2−、4−もしくは5−ピリミジニル、3−もしくは4−ピリダジニル、オルト−、メタ−もしくはパラ−ビフェニル、オルト−、メタ−もしくはパラ−ターフェニル、2−フルオレニル、2−スピロビフルオレニル、1−ナフチル、2−ナフチル、アントラセニル、フェニルアントラセニル、1−もしくは2−ナフチルアントラセニル、ビナフチル、ピレニル、フルオアンテニル、2−、3−、4−、5−、6−もしくは7−ベンゾアントラセニル、N−イミダゾリル、N−ベンゾイミダゾリル、フェニル−N−ベンゾイミダゾリル、N−フェニルベンゾイミダゾリル、フェニル−N−フェニルベンゾイミダゾリル、またはこれらの基の組み合わせからなる群より選択され、これらの各々は1以上の基R1で置換されていてもよいが、好ましくは非置換である、ことを特徴とする有機電子デバイス。
- 請求項1ないし6のいずれか1項による有機電子デバイスであって、すべての基Rは同じに選択される、ことを特徴とする有機電子デバイス。
- 請求項1ないし7のいずれか1項による有機電子デバイスであって、前記式(1)ないし(6)の化合物中のYは、pが0に等しくない場合、各々の出現において同一または異なっており、C(R1)2、NR1および5ないし14の芳香環原子を有する2価のアリールまたはヘテロアリール基からなる群より選択される2価の基を表し、1以上の基R1で置換されていてもよい、ことを特徴とする有機電子デバイス。
- 請求項1ないし8のいずれか1項による前記式(1)ないし(6)の化合物のうち1以上の化合物を含む少なくとも1つのオリゴマー、ポリマーまたはデンドリマーを含む有機電子デバイスであって、1以上の基Rは、前記式(1)ないし(6)の化合物からオリゴマー、ポリマーまたはデンドリマーへの結合を表す、有機電子デバイス。
- 請求項1ないし9のいずれか1項による有機エレクトロルミネセンスデバイスであって、アノード、カソードおよび1以上の発光層を含み、ここで少なくとも1つの有機層は前記式(1)ないし(6)の少なくとも1つの化合物または対応するオリゴマー、ポリマーもしくはデンドリマーを含み、さらに任意に、各々の場合に1以上の正孔注入層、正孔輸送層、正孔ブロッキング層、電子輸送層、電子注入層、電子ブロッキング層、エキシトンブロッキング層、電荷発生層および/または有機または無機p/n接合からなる群より選択されるさらなる層を含み、これらの層はドープされていてもよい、有機エレクトロルミネセンスデバイス。
- 請求項10による有機エレクトロルミネセンスデバイスであって、前記式(1)ないし(6)の少なくとも1つの化合物は、特に少なくとも1つの置換基R、好ましくは少なくとも2つの置換基R、特に好ましくはすべての3つの置換基Rが電子不足基を表す場合、正孔注入材料または正孔輸送材料として用いられる、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。
- 請求項11による有機エレクトロルミネセンスデバイスであって、前記置換基RはCN、F、NO2、CF3および置換または非置換の電子不足複素環からなる群より選択され、ここで前記電子不足複素環は、特に、ピリジン、ピラジン、ピリミジン、ピリダジン、トリアジン、ピロール、イミダゾール、トリアゾール、ベンゾイミダゾール、キノリン、イソキノリン、キノキサリン、チアジアゾール、チアゾールおよびオキサジアゾールからなる群より選択され、これらの各々は1以上の基R1で置換されていてもよい、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。
- 請求項10ないし12のいずれか1項による有機エレクトロルミネセンスデバイスであって、前記式(1)ないし(6)の化合物は、特に置換基Rが、各々の出現において同一または異なっており、芳香環系もしくは複素芳香環系を表す場合、電子輸送層または正孔ブロッキング層における電子輸送材料または正孔ブロッキング材料として用いられ、ここで前記電子輸送層または正孔ブロッキング層はドープされていてもよい、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。
- 請求項10ないし13のいずれか1項による有機エレクトロルミネセンスデバイスであって、前記式(1)ないし(6)の化合物は、電荷発生層における電荷発生材料として用いられる、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。
- 請求項1ないし14のいずれか1項による有機電子デバイスの製造方法であって、1以上の層を昇華法によって付ける、および/または1以上の層をOVPD(有機気相堆積)法またはキャリアガス昇華の助けによるOVPD法によって付ける、および/または1以上の層を溶液からおよび/または印刷法によって生じさせる、ことを特徴とする有機電子デバイスの製造方法。
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JP5677983B2 (ja) | 2015-02-25 |
US20110297925A1 (en) | 2011-12-08 |
TW201042001A (en) | 2010-12-01 |
CN102317408A (zh) | 2012-01-11 |
DE102009009277B4 (de) | 2023-12-07 |
WO2010094378A1 (de) | 2010-08-26 |
DE102009009277A1 (de) | 2010-08-19 |
KR20110134411A (ko) | 2011-12-14 |
CN102317408B (zh) | 2015-03-04 |
US9066410B2 (en) | 2015-06-23 |
KR101751544B1 (ko) | 2017-06-27 |
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