JP2019196351A - 正孔輸送化合物及びこれを含む有機発光素子 - Google Patents
正孔輸送化合物及びこれを含む有機発光素子 Download PDFInfo
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- JP2019196351A JP2019196351A JP2019087916A JP2019087916A JP2019196351A JP 2019196351 A JP2019196351 A JP 2019196351A JP 2019087916 A JP2019087916 A JP 2019087916A JP 2019087916 A JP2019087916 A JP 2019087916A JP 2019196351 A JP2019196351 A JP 2019196351A
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- Prior art keywords
- phenyl
- hole transport
- biphenyl
- mol
- light emitting
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 230000005525 hole transport Effects 0.000 title claims abstract description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 239000000126 substance Substances 0.000 claims description 11
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 99
- 239000013078 crystal Substances 0.000 abstract description 22
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 10
- 125000001769 aryl amino group Chemical group 0.000 abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 99
- 238000003786 synthesis reaction Methods 0.000 description 97
- 239000010410 layer Substances 0.000 description 93
- 239000000243 solution Substances 0.000 description 66
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 64
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 56
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 38
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 31
- 239000008096 xylene Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- -1 phenyl-9H-carbazol-3-yl Chemical group 0.000 description 27
- 239000000463 material Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002347 injection Methods 0.000 description 21
- 239000007924 injection Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 19
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- WPQJQVZDUZXMTO-UHFFFAOYSA-N 4-phenyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]aniline Chemical compound C=1C=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 WPQJQVZDUZXMTO-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000001771 vacuum deposition Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BTMPZEQJCZGPBG-UHFFFAOYSA-N N-(4-bromophenyl)-4-phenyl-N-[4-(9-phenylcarbazol-3-yl)phenyl]aniline Chemical compound BrC1=CC=C(C=C1)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C=1C=CC=2N(C3=CC=CC=C3C=2C=1)C1=CC=CC=C1 BTMPZEQJCZGPBG-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- ATKDFNSBYLLHRS-UHFFFAOYSA-N n-phenyl-4-(9-phenylcarbazol-3-yl)aniline Chemical compound C=1C=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=CC=1NC1=CC=CC=C1 ATKDFNSBYLLHRS-UHFFFAOYSA-N 0.000 description 5
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 4
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- KBEMKOZCBMQKMR-UHFFFAOYSA-N 4-phenyl-N-[4-(9-phenylpyrido[2,3-b]indol-6-yl)phenyl]aniline Chemical compound C1(=CC=CC=C1)N1C2=C(C3=CC(=CC=C13)C1=CC=C(C=C1)NC1=CC=C(C=C1)C1=CC=CC=C1)C=CC=N2 KBEMKOZCBMQKMR-UHFFFAOYSA-N 0.000 description 4
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 3
- JEYLGFCAZBGCMC-UHFFFAOYSA-N 3-(4-bromophenyl)-9-phenylcarbazole Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 JEYLGFCAZBGCMC-UHFFFAOYSA-N 0.000 description 3
- YMEKMYHKUIZEMG-UHFFFAOYSA-N 3-bromo-N-phenyl-N-[4-(9-phenylcarbazol-3-yl)phenyl]aniline Chemical compound BrC=1C=C(N(C2=CC=C(C=C2)C=2C=CC=3N(C4=CC=CC=C4C3C2)C2=CC=CC=C2)C2=CC=CC=C2)C=CC1 YMEKMYHKUIZEMG-UHFFFAOYSA-N 0.000 description 3
- BXABNPSQSDLRQU-UHFFFAOYSA-N 4-bromo-N-phenyl-N-[4-(9-phenylpyrido[2,3-b]indol-6-yl)cyclohexa-2,4-dien-1-yl]aniline Chemical compound C1C=C(C=CC1N(C2=CC=CC=C2)C3=CC=C(C=C3)Br)C4=CC5=C(C=C4)N(C6=C5C=CC=N6)C7=CC=CC=C7 BXABNPSQSDLRQU-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- GOWOMEQQPKLSNL-UHFFFAOYSA-N 3-(9-phenylcarbazol-3-yl)-N-(4-phenylphenyl)aniline Chemical compound C1=CC=C(C=C1)C2=CC=C(C=C2)NC3=CC=CC(=C3)C4=CC5=C(C=C4)N(C6=CC=CC=C65)C7=CC=CC=C7 GOWOMEQQPKLSNL-UHFFFAOYSA-N 0.000 description 2
- NORKENBPOCEOIW-UHFFFAOYSA-N 3-bromo-N-(4-phenylphenyl)-N-[4-(9-phenylpyrido[2,3-b]indol-6-yl)cyclohexa-2,4-dien-1-yl]aniline Chemical compound BrC=1C=C(C=CC1)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1C=CC(=CC1)C=1C=C2C3=C(N(C2=CC1)C1=CC=CC=C1)N=CC=C3 NORKENBPOCEOIW-UHFFFAOYSA-N 0.000 description 2
- ICNDBZRZHKGKSZ-UHFFFAOYSA-N 3-bromo-N-[4-(9-phenylcarbazol-3-yl)phenyl]-N-(4-phenylphenyl)aniline Chemical compound C1=CC=C(C=C1)C2=CC=C(C=C2)N(C3=CC=C(C=C3)C4=CC5=C(C=C4)N(C6=CC=CC=C65)C7=CC=CC=C7)C8=CC(=CC=C8)Br ICNDBZRZHKGKSZ-UHFFFAOYSA-N 0.000 description 2
- WEEIYQUSRPDUDD-UHFFFAOYSA-N 3-bromo-N-phenyl-N-(4-phenylphenyl)aniline Chemical compound BrC=1C=C(C=CC=1)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 WEEIYQUSRPDUDD-UHFFFAOYSA-N 0.000 description 2
- KZPLWFCMPRUBHF-UHFFFAOYSA-N 3-bromo-N-phenyl-N-[4-(9-phenylpyrido[2,3-b]indol-6-yl)cyclohexa-2,4-dien-1-yl]aniline Chemical compound C1C=C(C=CC1N(C2=CC=CC=C2)C3=CC(=CC=C3)Br)C4=CC5=C(C=C4)N(C6=C5C=CC=N6)C7=CC=CC=C7 KZPLWFCMPRUBHF-UHFFFAOYSA-N 0.000 description 2
- PQKGPULNKJWOEP-UHFFFAOYSA-N 4-N-(4-carbazol-9-ylphenyl)-1-N-[4-(9-phenylcarbazol-3-yl)phenyl]-1-N,4-N-bis(4-phenylphenyl)benzene-1,4-diamine Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C12)C1=CC=C(C=C1)N(C1=CC=C(C=C1)N(C1=CC=C(C=C1)C=1C=CC=2N(C3=CC=CC=C3C2C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 PQKGPULNKJWOEP-UHFFFAOYSA-N 0.000 description 2
- WQBYPHMQLOYLIG-UHFFFAOYSA-N 4-phenyl-N-[4-(5-phenylpyrido[3,2-b]indol-8-yl)phenyl]aniline Chemical compound C1=CC=C(C=C1)C2=CC=C(C=C2)NC3=CC=C(C=C3)C4=CC5=C(C=C4)N(C6=C5N=CC=C6)C7=CC=CC=C7 WQBYPHMQLOYLIG-UHFFFAOYSA-N 0.000 description 2
- UBASCOPZFCGGAV-UHFFFAOYSA-N 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 UBASCOPZFCGGAV-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- BTFIECQCKYNJTN-UHFFFAOYSA-N n-(4-bromophenyl)-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 BTFIECQCKYNJTN-UHFFFAOYSA-N 0.000 description 2
- MKKQYJZRYDUTNT-UHFFFAOYSA-N n-(4-bromophenyl)-n-phenyl-4-(9-phenylcarbazol-3-yl)aniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 MKKQYJZRYDUTNT-UHFFFAOYSA-N 0.000 description 2
- RRFNXQBSDBVPJA-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-phenylaniline Chemical compound C=1C=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 RRFNXQBSDBVPJA-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000000452 restraining effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 101500028161 Homo sapiens Tumor necrosis factor-binding protein 1 Proteins 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102400000089 Tumor necrosis factor-binding protein 1 Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002504 iridium compounds Chemical class 0.000 description 1
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- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005297 material degradation process Methods 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AFDFEVPHXYRVDH-UHFFFAOYSA-N n-(4-bromophenyl)-n,4-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 AFDFEVPHXYRVDH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-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
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Materials Engineering (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
2)蒸着過程で決定化が生じない高い転移温度
3)正孔の流れを円滑にするためのsp3カ−ボン構造の排除
以下、本発明による燐光ホスト用化合物を採った有機発光素子の構造及び製造方法について説明する。
合成例1
前記合成例で製造された化合物1乃至19(合成例16乃至34)に対する代表的物性を評価し、その結果を、下記表1に示す。
PLmax:スペクトロメ−タ及びサイクリックボルタンメトリ−から測定された物質の発光波長
HOMO LUMO バンドギャップ:スペクトロメ−タ及びサイクリックボルタンメトリ−から測定
T1:フィルム状で三重項エネルギ−(Triplet energy)(77Kで燐光測定を行って確認)
TID:物質の劣化温度(TGAを通じて確認)
Tg:ガラス転移温度
比較例
ITO基板は、発光面積が3mm×3mmのサイズとなるようにパタ−ニングした後、洗浄した。基板を真空チャンバに装着した後、ベ−ス圧力が1×10−6torrになるようにした後、アノ−ドITO上に、正孔注入物質でDNTPDを60nmの厚さで真空蒸着した。正孔輸送層として、BPBPAを30nmの厚さで成膜した。その後、前記正孔輸送層上に発光層としては、DBTTP1とド−パンドであるIr(ppy)3をド−パンドのド−ピング濃度10%で30nmの厚さで成膜した。その上に、電子輸送層として、ZADNを真空蒸着して、30nmの厚さで成膜し、電子注入層であるLiFを1.0nmの厚さで成膜した後、カソ−ドであるAlを100nmの厚さで成膜し、有機発光素子を製造して、発光特性を評価し、電流、電圧、及び輝度の相手変化をリアルタイムで測定して、素子の寿命を評価し、その結果を下記の表2に示している。
ITO基板は、発光面積が3mm×3mmのサイズとなるようにパタ−ニングした後、洗浄した。基板を真空チャンバに装着した後、ベ−ス圧力が1×10−6torrとなるようにした後、アノ−ドITO上に正孔注入物質でDNTPDを60nmの厚さで真空蒸着した。正孔輸送層として、前記化合物1乃至19(合成例16乃至34により製造された化合物)を30nmの厚さで成膜した。その後、前記正孔輸送層上に、発光層として、DBTTP1とド−パンドであるIr(ppy)3をド−パンドのド−ピング濃度10%で30nmの厚さで成膜した。その上に、電子輸送層として、ZADNを真空蒸着して30nmの厚さで成膜し、電子注入層であるLiFを1.0nmの厚さで成膜した後、カソ−ドであるAlを100nmの厚さで成膜し、有機発光素子を製造して、発光特性を評価し、電流、電圧、及び輝度の相手変化をリアルタイムで測定して素子の寿命を評価し、その結果を下記の表2に示している。
20:アノ−ド電極
30:正孔注入層
40:正孔輸送層
50:発光層
60:電子輸送層
70:電子注入層
80:カソ−ド電極
Claims (5)
- 一対の電極の間に正孔輸送層を含む有機発光素子において、
前記正孔輸送層が、請求項1乃至4のいずれか一項による正孔輸送化合物を含むことを特徴とする有機発光素子。
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KR1020180052352A KR102032125B1 (ko) | 2018-05-08 | 2018-05-08 | 정공수송 화합물 및 이를 포함한 유기 발광 소자 |
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TW (1) | TWI735871B (ja) |
Citations (14)
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CN110452154A (zh) | 2019-11-15 |
KR102032125B1 (ko) | 2019-10-15 |
TW201947009A (zh) | 2019-12-16 |
JP6776401B2 (ja) | 2020-10-28 |
CN110452154B (zh) | 2023-03-31 |
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