JP5619418B2 - 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP5619418B2 JP5619418B2 JP2009522494A JP2009522494A JP5619418B2 JP 5619418 B2 JP5619418 B2 JP 5619418B2 JP 2009522494 A JP2009522494 A JP 2009522494A JP 2009522494 A JP2009522494 A JP 2009522494A JP 5619418 B2 JP5619418 B2 JP 5619418B2
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- phenanthrolin
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- 239000000463 material Substances 0.000 title claims description 70
- 238000005401 electroluminescence Methods 0.000 title claims description 20
- -1 9-carbazolyl group Chemical group 0.000 claims description 1406
- 125000001424 substituent group Chemical group 0.000 claims description 293
- 125000004432 carbon atom Chemical group C* 0.000 claims description 287
- 125000003118 aryl group Chemical group 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000004104 aryloxy group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001769 aryl amino group Chemical group 0.000 claims description 20
- 125000005110 aryl thio group Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 16
- 239000010409 thin film Substances 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000004696 coordination complex Chemical class 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001721 carbon Chemical class 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 84
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000010408 film Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 125000003373 pyrazinyl group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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 compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 230000007547 defect Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 6
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 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 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- 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 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 125000006083 1-bromoethyl group Chemical group 0.000 description 5
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 230000002950 deficient Effects 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 4
- 125000005999 2-bromoethyl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000005997 bromomethyl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910018068 Li 2 O Inorganic materials 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 208000027386 essential tremor 1 Diseases 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 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
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006481 2-iodobenzyl group Chemical group [H]C1=C([H])C(I)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 2
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 2
- 125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 2
- 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 description 2
- 125000005803 6,12-chrysenylene group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C1=C([H])C([*:2])=C3C([H])=C([H])C([H])=C([H])C3=C1C([H])=C2[*:1] 0.000 description 2
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- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ZGEUUNNIQMDTKF-UHFFFAOYSA-N c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)cc(c2c3)c1[o]c2ccc3-c1cccc(-c(cc2)cc(c3c4)c2[o]c3ccc4-[n]2c(cccc3)c3c3c2cccc3)c1 Chemical compound c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)cc(c2c3)c1[o]c2ccc3-c1cccc(-c(cc2)cc(c3c4)c2[o]c3ccc4-[n]2c(cccc3)c3c3c2cccc3)c1 ZGEUUNNIQMDTKF-UHFFFAOYSA-N 0.000 description 1
- JAZRWCXJBSAPAX-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3)c1[o]c2ccc3-c1cc(-[n]2c(cccc3)c3c3c2cccc3)cc(-c(cc2)cc(c3c4)c2[o]c3ccc4-[n]2c3ccccc3c3ccccc23)c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3)c1[o]c2ccc3-c1cc(-[n]2c(cccc3)c3c3c2cccc3)cc(-c(cc2)cc(c3c4)c2[o]c3ccc4-[n]2c3ccccc3c3ccccc23)c1 JAZRWCXJBSAPAX-UHFFFAOYSA-N 0.000 description 1
- BTWMVHCHCIKCFN-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3)c1[o]c2ccc3-c1ccc2[o]c(ccc(-c(cc3c4c5)ccc3[o]c4ccc5-[n]3c4ccccc4c4c3cccc4)c3)c3c2c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3)c1[o]c2ccc3-c1ccc2[o]c(ccc(-c(cc3c4c5)ccc3[o]c4ccc5-[n]3c4ccccc4c4c3cccc4)c3)c3c2c1 BTWMVHCHCIKCFN-UHFFFAOYSA-N 0.000 description 1
- RVTIVZGTWIWFBJ-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3)c1[o]c2ccc3-c1cccc(-c2cc(-c(cc3)cc(c4c5)c3[o]c4ccc5-[n]3c4ccccc4c4c3cccc4)ccc2)c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3)c1[o]c2ccc3-c1cccc(-c2cc(-c(cc3)cc(c4c5)c3[o]c4ccc5-[n]3c4ccccc4c4c3cccc4)ccc2)c1 RVTIVZGTWIWFBJ-UHFFFAOYSA-N 0.000 description 1
- MHNWAHQEJWJENQ-UHFFFAOYSA-N c1cc(-c(cc2)cc(c3c4)c2[o]c3ccc4-[n]2c3ccncc3c3c2ccnc3)cc(-c(cc2c3c4)ccc2[o]c3ccc4-[n]2c3ccncc3c3c2ccnc3)c1 Chemical compound c1cc(-c(cc2)cc(c3c4)c2[o]c3ccc4-[n]2c3ccncc3c3c2ccnc3)cc(-c(cc2c3c4)ccc2[o]c3ccc4-[n]2c3ccncc3c3c2ccnc3)c1 MHNWAHQEJWJENQ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 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
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical group C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- KELCFVWDYYCEOQ-UHFFFAOYSA-N phenanthridin-1-ol Chemical compound C1=CC=CC2=C3C(O)=CC=CC3=NC=C21 KELCFVWDYYCEOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical group C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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Description
特許文献7,8には、ジベンゾ化合物にカルバゾリル骨格を結合させた化合物群が記載されている。青色系りん光素子のホスト材料として実施例に記載されているが、本発明のような化合物群に関しては記載が無く、効果も不明である。
特許文献9,10,11には同様にジベンゾ化合物とアントラセン骨格との結合化合物が記載されている。しかしながらこれらの化合物はアントラセン骨格を有しているため,3重項の励起状態のエネルギーレベルが小さく,これらの化合物群のどれを発光層のホスト材料として用いても,青色系りん光発光材料を発光させることができない。
また,特許文献12には少なくとも2つの重合性官能基が必須であるジベンゾフラン骨格を有する化合物が記載されている。しかし、2重結合、3重結合等の不飽和結合で置き換えられることにより形成される基,例えば、プロペニレン基、ビニレン基、4−プロピル−2−ペンテニレン基等のような重合性置換基をりん光発光素子のホスト材料の分子骨格に組み込んだ場合,素子内でラジカルが連鎖的に発生し,発光効率,寿命に悪い影響を及ぼすことが懸念される。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7〜R9は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7が互いに結合して環構造を形成しない場合、R7〜R9の少なくとも1つは置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいフェニル基、置換基を有してもよいジベンゾフラニル基、または、置換基を有してもよいジベンゾチオフェニル基であり、
R8とR9またはR8とR7は互いに結合して置換基を有してもよい環構造を形成してもよく、該環構造を形成しないR7またはR9は水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7とそれらが結合しているベンゼン環がカルバゾリル基を形成する場合は除く、
R1〜R3およびR6〜R10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。
R7〜R9は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である。但し、R8とR9またはR8とR7が互いに結合して環構造を形成しない場合、R7〜R9の少なくとも1つは置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいフェニル基、置換基を有してもよいジベンゾフラニル基、または、置換基を有してもよいジベンゾチオフェニル基である。
前記アルカリ土類金属としては、Ca(仕事関数:2.9eV)、Sr(仕事関数:2.0〜2.5eV)、Ba(仕事関数:2.52eV)等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
前記希土類金属としては、Sc、Y、Ce、Tb、Yb等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
以上の金属のうち好ましい金属は特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子の発光輝度の向上や長寿命化が可能になる。
前記アルカリ土類金属化合物としては、BaO、SrO、CaO及びこれらを混合したBaxSr1-xO(0<x<1)、BaxCa1-xO(0<x<1)等が挙げられ、BaO、SrO、CaOが好ましい。
前記希土類金属化合物としては、YbF3、ScF3、ScO3、Y2O3、Ce2O3、GdF3、TbF3等が挙げられ、YbF3、ScF3、TbF3が好ましい。
還元性ドーパントを層状に形成する場合は、界面の有機層を発光材料や電子注入材料により層状に形成した後に、還元ドーパントを単独で抵抗加熱蒸着法により蒸着し、好ましくは層の厚み0.1〜15nmで形成する。
還元性ドーパントを島状に形成する場合は、界面の有機層を発光材料や電子注入材料により島状に形成した後に、還元ドーパントを単独で抵抗加熱蒸着法により蒸着し、好ましくは島の厚み0.05〜1nmで形成する。
また、本発明の有機EL素子における、主成分である発光材料や電子注入材料と還元性ドーパントの割合としては、モル比で主成分:還元性ドーパント=5:1〜1:5であると好ましく、2:1〜1:2であるとさらに好ましい。
ハロゲン原子の例としては、前記と同様のものが挙げられる。また、置換されていてもよいアミノ基の例としては、前記アルキルアミノ基、アリールアミノ基、アラルキルアミノ基と同様のものが挙げられる。
炭素数1〜40の炭化水素基としては、アルキル基、アルケニル基、シクロアルキル基、アルコキシ基、アリール基、複素環基、アラルキル基、アリールオキシ基、アルコキシカルボニル基等が挙げられ、それぞれ置換されていてもよい。該アルキル基、アルケニル基、シクロアルキル基、アルコキシ基、アリール基、複素環基、アラルキル基、およびアリールオキシ基の例としては、前記と同様のものが挙げられ、アルコキシカルボニル基は−COOY’と表され、Y’の例としては前記アルキル基と同様のものが挙げられる。
式(A)のLは、下記一般式(A’)又は(A'')で表される基である。
LBがアリール基または芳香族複素環基である場合、置換基を有していてもよい。該置換基としては、好ましくはアルキル基、アルケニル基、アルキニル基、アリール基、アミノ基、アルコキシ基、アリールオキシ基、アシル基、アルコキシカルボニル基、アリールオキシカルボニル基、アシルオキシ基、アシルアミノ基、アルコキシカルボニルアミノ基、アリールオキシカルボニルアミノ基、スルホニルアミノ基、スルファモイル基、カルバモイル基、アルキルチオ基、アリールチオ基、スルホニル基、ハロゲン原子、シアノ基、芳香族複素環基であり、より好ましくはアルキル基、アリール基、アルコキシ基、アリールオキシ基、ハロゲン原子、シアノ基、芳香族複素環基であり、さらに好ましくはアルキル基、アリール基、アルコキシ基、アリールオキシ基、芳香族複素環基であり、特に好ましくはアルキル基、アリール基、アルコキシ基、芳香族複素環基である。
RB2の脂肪族炭化水素基は、直鎖、分岐又は環状のアルキル基(好ましくは炭素数1〜20、より好ましくは炭素数1〜12、特に好ましくは炭素数1〜8のアルキル基であり、例えば、メチル、エチル、イソプロピル、t−ブチル、n−オクチル、n−デシル、n−ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシル等が挙げられる。)、アルケニル基(好ましくは炭素数2〜20、より好ましくは炭素数2〜12、特に好ましくは炭素数2〜8のアルケニル基であり、例えば、ビニル、アリル、2−ブテニル、3−ペンテニル等が挙げられる。)、アルキニル基(好ましくは炭素数2〜20、より好ましくは炭素数2〜12、特に好ましくは炭素数2〜8のアルキニル基であり、例えば、プロパルギル、3−ペンチニル等が挙げられる。)であり、アルキル基であると好ましい。
RB2として好ましくは脂肪族炭化水素基、アリール基又は複素環基であり、より好ましくは脂肪族炭化水素基又はアリール基(好ましくは炭素数6〜30、より好ましくは炭素数6〜20、さらに好ましくは炭素数6〜12)であり、さらに好ましくは脂肪族炭化水素基(好ましくは炭素数1〜20、より好ましくは炭素数1〜12、さらに好ましくは炭素数2〜10)である。
nB2は、1〜6の整数、好ましくは1〜4の整数、より好ましくは2または3である。
ZB71、ZB72及びZB73は、それぞれ一般式(B)におけるZB2と同様であり、また好ましい範囲も同様である。
LB71、LB72及びLB73は、それぞれ単結合または一般式(B)における二価のLBと同様であり、好ましくは、単結合、二価の芳香族炭化水素環基、二価の芳香族複素環基、及びこれらの組み合わせからなる二価の連結基であり、より好ましくは単結合である。LB71、LB72及びLB73は置換基を有していてもよく、置換基としては前記一般式(B)におけるLBで表される基の置換基として挙げたものと同様であり、また好ましい置換基も同様である。
Yは、窒素原子、1,3,5−ベンゼントリイル基又は2,4,6−トリアジントリイル基を表す。1,3,5−ベンゼントリイル基は2,4,6−位に置換基を有していてもよく、置換基としては、例えば、アルキル基、芳香族炭化水素環基、ハロゲン原子などが挙げられる。
また、本発明における電子注入層は、前述の還元性ドーパントを含有していても好ましい。
本発明の有機EL素子の各有機層の膜厚は特に制限されないが、一般に膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い印加電圧が必要となり効率が悪くなるため、通常は数nmから1μmの範囲が好ましい。
化合物No.4の合成
(1)2,8-dibromodibenzofuranの合成
FDマススペクトル分析
C12H6Br2O:理論値325.6、観測値326
(2)2-bromo-8-carbazolyldibenzofuranの合成
FDマススペクトル分析
C24H14BrNO:理論値412.3、観測値412
(3)化合物No.4の合成
FDマススペクトル分析
C42H26N2O:理論値574.67、観測値574
化合物No.9の合成
FDマススペクトル分析
C54H33N3O:理論値739.9、観測値739
化合物No.10の合成
FDマススペクトル分析
C42H25NO2:理論値575.7、観測値575
化合物No.12の合成
FDマススペクトル分析
C54H32N2O2:理論値740.84、観測値740
装置:HX110(日本電子社製)
条件:加速電圧 8kV
スキャンレンジ m/z=50〜1500
エミッタ種:カーボン
エミッタ電流:0mA→2mA/分→40mA(10分保持)
(有機EL素子の作製)
25mm×75mm×1.1mm厚のITO透明電極付きガラス基板(旭硝子製)をイソプロピルアルコール中で5分間超音波洗浄した後、30分間UVオゾン洗浄した。洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に、前記透明電極を覆うようにして膜厚80nmのHTM1(下記構造式参照)膜を抵抗加熱により成膜した。該HTM1膜は正孔輸送/正孔注入層として機能する。引き続いて、該HTM1膜上に、ホスト化合物として化合物No.4およびドーパント化合物として錯体K−21を含む膜厚30nmの共蒸着膜を抵抗加熱により成膜した。錯体K−21の濃度は7.5wt%であった。この共蒸着膜は発光層として機能する。引き続き、該発光層上に膜厚10nmのETM1膜、該ETM1膜上に膜厚20nmのETM2膜を積層成膜した。該ETM1膜及びETM2膜はそれぞれ第一及び第二電子輸送層として機能する。次いで、成膜速度0.1Å/minで膜厚0.5nmのLiF電子注入性電極(陰極)を形成した。このLiF層上に金属Alを蒸着させ、膜厚150nmの金属陰極を形成し有機EL素子を得た。
以上のように作製した有機EL素子を直流電流駆動により発光させ、発光波長(λ)、輝度(L)、電流密度を測定し、電流効率(L/J)を求めた。電流密度1mA/cm2時の結果を表1に示す。
実施例1においてホスト化合物No.4を用いる代わりに表1に記載のホスト材料を用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表1に示す。
実施例1においてホスト化合物No.4を用いる代わりにホスト材料としてCBPを用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表1に示す。
実施例1においてホスト化合物No.4を用いる代わりにホスト材料として国際公開特許WO2005−113531号公報記載の下記化合物X−1を用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表1に示す。
(正孔輸送層への応用)
実施例1において正孔輸送/正孔注入層としてHTM1の代わりに表2に記載の化合物を用い、ホスト材料として下記H−1を用いた以外は実施例1と同様にして有機EL素子を作製した。発光性能評価結果を表2に示す。
Claims (13)
- 下記一般式(1)で表される化合物からなる、少なくとも1種のりん光発光性の金属錯体とともに用いる有機エレクトロルミネッセンス素子用材料。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7〜R9は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、
但し、R8とR9またはR8とR7が互いに結合して環構造を形成しない場合、R7〜R9の少なくとも1つは置換基を有してもよい9−カルバゾリル基、置換基を有してもよい窒素原子数2〜5のアザカルバゾリル基、置換基を有してもよいフェニル基(但し、当該フェニル基が有してもよい置換基は、炭素数1〜8のアルキル基、炭素数1〜5個のヒドロキシアルキル基、炭素数1〜4個のハロアルキル基、炭素数1〜4個のアミノアルキル基、炭素数1〜4個のシアノアルキル基、炭素数1〜5個のニトロアルキル基、炭素数3〜10個の(アルキル)シクロアルキル基、炭素数1〜6のアルコキシ基、炭素数3〜6のシクロアルコキシ基、核原子数5〜40のアリール基、核原子数5〜40のアリール基で置換されたアミノ基、核原子数5〜40のアリール基を有するエステル基、炭素数1〜6のアルキル基を有するエステル基、シアノ基、ニトロ基、ハロゲン原子、ヒドロキシル基、アミノ基、及び、置換又は無置換のカルバゾリル基からなる群より選ばれる基である)、置換基を有してもよい1−ジベンゾフラニル基、置換基を有してもよい3−ジベンゾフラニル基、置換基を有してもよい4−ジベンゾフラニル基、置換基を有してもよい1−ジベンゾチオフェニル基、置換基を有してもよい3−ジベンゾチオフェニル基、または、置換基を有してもよい4−ジベンゾチオフェニル基であり、
R8とR9またはR8とR7は互いに結合して置換基を有してもよい環構造を形成してもよく(但し、当該環構造は、R 8 とR 9 またはR 8 とR 7 が結合しているベンゼン環と共に、窒素原子数2〜5のアザカルバゾール構造又はフルオレン構造を形成する場合に限る)、
該環構造を形成しないR7またはR9は水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、但し、R8とR9またはR8とR7とそれらが結合しているベンゼン環がカルバゾリル基を形成する場合は除く、
R1〜R3およびR6〜R10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である。] - 下記一般式(2)で表される化合物からなる、少なくとも1種のりん光発光性の金属錯体とともに用いる有機エレクトロルミネッセンス素子用材料。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7とR8は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基であり、R8とR7は互いに結合して置換基を有してもよい環構造を形成してもよい(但し、R8とR7とそれらが結合しているベンゼン環がカルバゾリル基を形成する場合は除く)、
但し、R7、R8、およびR20〜R24の少なくとも1つが置換又は無置換の9−カルバゾリル基、無置換のジベンゾフラニル基、置換又は無置換の窒素原子数2〜5のアザカルバゾリル基、および無置換のジベンゾチオフェニル基から選ばれた置換基であり、
R1〜R3およびR6〜R8、R10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。 - 下記一般式(3)で表される化合物からなる、少なくとも1種のりん光発光性の金属錯体とともに用いる有機エレクトロルミネッセンス素子用材料。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7とR9は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、
但し、R7、R9、およびR20〜R24の少なくとも1つが、置換又は無置換の9−カルバゾリル基、置換又は無置換のジベンゾフラニル基、置換又は無置換の窒素原子数2〜5のアザカルバゾリル基、および置換又は無置換のジベンゾチオフェニル基から選ばれた置換基であり、
R1〜R3、R6、R7、R9、およびR10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。 - 下記一般式(4)で表される化合物からなる、少なくとも1種のりん光発光性の金属錯体とともに用いる有機エレクトロルミネッセンス素子用材料。
R6は、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7は、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基である、
但し、R7およびR21〜R23の少なくとも1つが、置換又は無置換の9−カルバゾリル基、置換又は無置換のジベンゾフラニル基、置換又は無置換の窒素原子数2〜5のアザカルバゾリル基、および置換又は無置換のジベンゾチオフェニル基から選ばれた置換基であり、
R1〜R3、R6、およびR7の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。 - 下記一般式(5)で表される化合物からなる、少なくとも1種のりん光発光性の金属錯体とともに用いる有機エレクトロルミネッセンス素子用材料。
R6とR10は、それぞれ独立に、水素原子または置換基を有してもよい炭素数1〜40のアルキル基であり、
R7とR8は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜40のアルキル基、置換基を有してもよい炭素数3〜15のシクロアルキル基、置換基を有してもよい炭素数3〜20の複素環基、置換基を有してもよい炭素数1〜40のアルコキシ基、置換基を有してもよい炭素数6〜40の非縮合アリール基、置換基を有してもよい炭素数10〜18の縮合アリール基、置換基を有してもよい炭素数6〜20のアリールオキシ基、置換基を有してもよい炭素数7〜20のアラルキル基、置換基を有してもよい炭素数6〜40のアリールアミノ基、置換基を有してもよい炭素数1〜40のアルキルアミノ基、置換基を有してもよい炭素数7〜60のアラルキルアミノ基、置換基を有してもよい炭素数7〜40のアリールカルボニル基、置換基を有してもよい炭素数6〜20のアリールチオ基、置換基を有してもよい炭素数1〜40のハロゲン化アルキル基、または、シアノ基であり、R8とR7は互いに結合して置換基を有してもよい環構造を形成してもよく(但し、R8とR7とそれらが結合しているベンゼン環がカルバゾリル基を形成する場合は除く)、
但し、R7、R8、R20、およびR22〜R29の少なくとも1つが、置換又は無置換の9−カルバゾリル基、置換又は無置換のジベンゾフラニル基、置換又は無置換の窒素原子数2〜5のアザカルバゾリル基、および置換又は無置換のジベンゾチオフェニル基から選ばれた置換基であり、
R1〜R3、R6〜R8、およびR10の各置換基は末端に重合性官能基を有することはなく、
Xは、硫黄原子または酸素原子である]。 - 陰極と陽極間に一層又は複数層からなる有機薄膜層が挟持されており、該有機薄膜層の少なくとも1層が少なくとも1種のりん光発光性の金属錯体とともに用いるホスト材料を含有する発光層であり、該有機薄膜層の少なくとも一層が請求項1〜5のいずれか一項に記載の有機エレクトロルミネッセンス素子用材料を含有する有機エレクトロルミネッセンス素子。
- 前記発光層が含有するホスト材料が前記有機エレクトロルミネッセンス素子用材料である請求項6記載の有機エレクトロルミネッセンス素子。
- 前記発光層がホスト材料とりん光性の発光材料を含有し、該ホスト材料が前記有機エレクトロルミネッセンス素子用材料である請求項6記載の有機エレクトロルミネッセンス素子。
- 前記りん光性の発光材料がイリジウム(Ir)、オスミウム(Os)又は白金(Pt)金属を含有する化合物である請求項8記載の有機エレクトロルミネッセンス素子。
- 前記発光層の発光波長の最大ピーク波長が500nm以下である青色系金属錯体を含有する請求項8記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層の少なくとも1層が電子注入層であり、該電子注入層が、前記有機エレクトロルミネッセンス素子用材料とは異なる含窒素環誘導体を主成分として含有する請求項6記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層の少なくとも1層が正孔輸送層であり、該正孔輸送層が前記有機エレクトロルミネッセンス素子用材料を含有する請求項6記載の有機エレクトロルミネッセンス素子。
- 陰極と有機薄膜層との界面領域に還元性ドーパントが添加されてなる請求項6記載の有機エレクトロルミネッセンス素子。
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EP2166583A4 (en) | 2011-10-19 |
JPWO2009008100A1 (ja) | 2010-09-02 |
WO2009008100A1 (ja) | 2009-01-15 |
KR20100031736A (ko) | 2010-03-24 |
US20090017331A1 (en) | 2009-01-15 |
KR101453128B1 (ko) | 2014-10-27 |
WO2009008099A1 (ja) | 2009-01-15 |
EP2166584A4 (en) | 2011-10-26 |
TW200902675A (en) | 2009-01-16 |
EP2166583A1 (en) | 2010-03-24 |
EP2166584B1 (en) | 2016-06-08 |
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US20120097937A1 (en) | 2012-04-26 |
JPWO2009008099A1 (ja) | 2010-09-02 |
US20090017330A1 (en) | 2009-01-15 |
EP2166584A1 (en) | 2010-03-24 |
US7968213B2 (en) | 2011-06-28 |
US8114530B2 (en) | 2012-02-14 |
KR20100032888A (ko) | 2010-03-26 |
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