JP7379601B2 - リン光発光ダイオード中の単一トリフェニレン発色団 - Google Patents
リン光発光ダイオード中の単一トリフェニレン発色団 Download PDFInfo
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- JP7379601B2 JP7379601B2 JP2022111772A JP2022111772A JP7379601B2 JP 7379601 B2 JP7379601 B2 JP 7379601B2 JP 2022111772 A JP2022111772 A JP 2022111772A JP 2022111772 A JP2022111772 A JP 2022111772A JP 7379601 B2 JP7379601 B2 JP 7379601B2
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- Prior art keywords
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- triphenylene
- organic
- mmol
- organic layer
- Prior art date
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 title description 92
- 125000005580 triphenylene group Chemical group 0.000 title description 80
- 239000010410 layer Substances 0.000 claims description 171
- 239000002019 doping agent Substances 0.000 claims description 55
- 239000012044 organic layer Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
- 239000000463 material Substances 0.000 description 150
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 229910052757 nitrogen Inorganic materials 0.000 description 40
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- 239000000243 solution Substances 0.000 description 36
- -1 triphenylene compound Chemical class 0.000 description 32
- 230000032258 transport Effects 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 24
- 239000000758 substrate Substances 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- 238000004770 highest occupied molecular orbital Methods 0.000 description 18
- 150000003384 small molecules Chemical class 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 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 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002800 charge carrier Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000011241 protective layer Substances 0.000 description 12
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000011368 organic material Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000005693 optoelectronics Effects 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 230000005281 excited state Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 6
- 229920000736 dendritic polymer Polymers 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- 150000003643 triphenylenes Chemical group 0.000 description 6
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 6
- 235000019798 tripotassium phosphate Nutrition 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 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 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001475 halogen functional group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 238000010129 solution processing Methods 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- QUGJLZNUGVQTGP-UHFFFAOYSA-N (3-triphenylen-2-ylphenyl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 QUGJLZNUGVQTGP-UHFFFAOYSA-N 0.000 description 4
- XIWWHUAOOZIREN-UHFFFAOYSA-N 1-bromotriphenylene Chemical group C1=CC=CC2=C3C(Br)=CC=CC3=C(C=CC=C3)C3=C21 XIWWHUAOOZIREN-UHFFFAOYSA-N 0.000 description 4
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000002207 thermal evaporation Methods 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 3
- RSWOJEDGRFCGFR-UHFFFAOYSA-N 2,3,6,7,10,11-hexakis-phenyltriphenylene Chemical group C1=CC=CC=C1C1=CC(C2=CC(=C(C=3C=CC=CC=3)C=C2C2=CC(=C(C=3C=CC=CC=3)C=C22)C=3C=CC=CC=3)C=3C=CC=CC=3)=C2C=C1C1=CC=CC=C1 RSWOJEDGRFCGFR-UHFFFAOYSA-N 0.000 description 3
- KXIFXZJZTKQHDW-UHFFFAOYSA-N 2-(3-methoxyphenyl)triphenylene Chemical group COC1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 KXIFXZJZTKQHDW-UHFFFAOYSA-N 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- SCZWJXTUYYSKGF-UHFFFAOYSA-N 5,12-dimethylquinolino[2,3-b]acridine-7,14-dione Chemical compound CN1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 SCZWJXTUYYSKGF-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
- PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 2
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 2
- ZGHQUYZPMWMLBM-UHFFFAOYSA-N 1,2-dichloro-4-phenylbenzene Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 ZGHQUYZPMWMLBM-UHFFFAOYSA-N 0.000 description 2
- PBPZUKVOJHAPEH-UHFFFAOYSA-N 1-bromo-3,5-bis(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC(Br)=CC(C=2C=CC(C)=CC=2)=C1 PBPZUKVOJHAPEH-UHFFFAOYSA-N 0.000 description 2
- GTPBIVBFUOMIBT-UHFFFAOYSA-N 2,11-dimethoxytriphenylene Chemical group C1=C(OC)C=C2C3=CC(OC)=CC=C3C3=CC=CC=C3C2=C1 GTPBIVBFUOMIBT-UHFFFAOYSA-N 0.000 description 2
- CLVUPEHHVNFPFQ-UHFFFAOYSA-N 2-[3-(3-methoxyphenyl)phenyl]triphenylene Chemical group COC1=CC=CC(C=2C=C(C=CC=2)C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 CLVUPEHHVNFPFQ-UHFFFAOYSA-N 0.000 description 2
- GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- OVENNPHGLUWCOK-UHFFFAOYSA-N 3-(3-triphenylen-2-ylphenyl)phenol Chemical compound OC1=CC=CC(C=2C=C(C=CC=2)C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 OVENNPHGLUWCOK-UHFFFAOYSA-N 0.000 description 2
- CGBWLVNDAHMWGP-UHFFFAOYSA-N 3-triphenylen-2-ylphenol Chemical compound OC1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 CGBWLVNDAHMWGP-UHFFFAOYSA-N 0.000 description 2
- VXLBBSLCTFTKOE-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-triphenylen-2-yl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC=CC=2)C=2C3=CC=CC=2)C3=C1 VXLBBSLCTFTKOE-UHFFFAOYSA-N 0.000 description 2
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 101100232347 Mus musculus Il11ra1 gene Proteins 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- QCXCWYLMYITISZ-UHFFFAOYSA-N [3-(3-triphenylen-2-ylphenyl)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC(C=2C=C(C=CC=2)C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 QCXCWYLMYITISZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
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Description
本明細書で用いるように、材料をいう略語は以下のとおりである。
CBP: 4,4’-N,N-ジカルバゾール-ビフェニル
m-MTDATA: 4,4’,4’’-トリス(3-メチルフェニルフェニルアミノ)トリフェニルアミン
Alq3: 8-トリス-ヒドロキシキノリンアルミニウム
Bphen: 4,7-ジフェニル-1,10-フェナントロリン
n-BPhen: n-ドープ型BPhen(リチウムでドープ)
F4-TCNQ: テトラフルオロ-テトラシアノ-キノジメタン
p-MTDATA: p-ドープ型m-MTDATA(F4-TCNQでドープ)
Ir(ppy)3: トリス(2-フェニルピリジン)イリジウム
Ir(ppz)3: トリス(1-フェニルピラゾロト,N,C(2’)イリジウム(III)
BCP: 2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン
TAZ: 3-フェニル-4-(1’-ナフチル)-5-フェニル-1,2,4-トリアゾール
CuPc: 銅フタロシアニン
ITO: インジウムスズオキシド
NPD: N,N’-ジフェニル-N,N’-ジ(1-ナフチル)-ベンジジン
TPD: N,N’-ジフェニル-N,N’-ジ(3-トリル)-ベンジジン
BAlq: アルミニウム(III)ビス(2-メチル-8-ヒドロキシキノリナート)4-フェニルフェノラート
mCP: 1,3-N,N-ジカルバゾール-ベンゼン
DCM: 4-(ジシアノエチレン)-6-(4-ジメチルアミノスチリル-2-メチル)-4H-ピラン
DMQA: N,N’-ジメチルキナクリドン
PEDOT:PSS: ポリ(3,4-エチレンジオキシチオフェン)とポリスチレンスルホネート(PSS)の水性分散物
HPT: 2,3,6,7,10,11-ヘキサフェニルトリフェニレン
2,7-DCP: 2,7-N,N-ジカルバゾールフェナントレン
3,3’-DC-o-TerP: 3,3’-ジカルバゾール-o-ターフェニル
4,4’-DC-o-TerP: 4,4’-ジカルバゾール-o-ターフェニル
2,6’-DCN: 2,6-N,N-ジカルバゾールナフタレン
Ir(5-Phppy)3: トリス[5’-フェニル(2-フェニルピリジン)]イリジウム(III)
Ir(3-Meppy)3: トリス(3-メチル-2-フェニルピリジン)イリジウム(III)
Ir(1-piq)3: トリス(1-フェニルイソキノリン)イリジウム(III)
Ir(3-Mepq)2(acac): ビス(3-メチル-2-フェニルキノリン)イリジウム(III)アセチルアセトナート
Ir(5-Phppy)3: トリス[5-フェニル(2-フェニルピリジン)]イリジウム(III)
Ir(pq)2(acac): ビス(2-フェニルキノリン)イリジウム(III)アセチルアセトナート
2,2-BT: 2,2-ビストリフェニレン
HPT: 2,3,6,7,10,11-ヘキサフェニルトリフェニレン
H1NT: 2,3,6,7,10,11-ヘキサ(1-ナフチル)トリフェニレン
H2BT: 2,3,6,7,10,11-ヘキサ(2-ビフェニル)トリフェニレン
混合物からカラムクロマトグラフィーによって容易に精製することができる。対して、対応するジ置換物質からの4,4,5,5-テトラメチル-2-(トリフェニレン-2-イル)-1,3,2-ジオキサボロランの分離はずっと困難であって時間もかかることが、実際問題としてわかっている。したがって、3-(トリフェニレン-2-イル)フェニルトリフルオロメタンスルホネートのためのこの合成経路は、高純度のトリフェニレン系オプトエレクトロニクス材料を得るために有利である。
1,2-ジブロモベンゼン(50 g, 212 mmol)、4-メトキシフェニルボロン酸(78 g, 513 mmol)、トリフェニルホスフィン(11.12 g, 42.2 mmol)、炭酸カリウム(73.25 g, 530 mmol)、ジメトキシエタン(290 mL)、及び水(290 mL)からなる混合物を調製した。20分間、この混合物中に窒素を直接バブリングさせた。酢酸パラジウム(4.76 g, 21.2 mmol)を添加し、混合物を夜通し窒素下で加熱し還流させた。反応混合物を冷やし、水及びジクロロメタンを添加した。層を分離し、水層をジクロロメタンで抽出した。一緒にした有機層を、セライトを通してろ過し、食塩水で洗い、硫酸マグネシウム上で乾燥させ、ろ過し、溶媒を蒸発させて黒色オイルを得た。この粗製物質を0から100%のジクロロメタン/ヘキサンで溶離するクロマトグラフィーによって精製した。最もきれいな画分を、クーゲルロール(Kugelrohr)を使用して200~220℃での蒸留によって精製した。生成物は煮沸フラスコ中に残り、かついくらかの生成物と一緒にバルブ中に不純物が蒸留された。49 g(80%)のきれいな生成物が得られた。
12.4 g(42.7 mmol)の4,4’-ジメトキシ-o-ターフェニル及び16 g(63.0 mmol)のヨウ素片を250 mLの反応容器中に入れた。200 mLのトルエンを添加し、次に30 mLのプロピレンオキシドを添加した。再循環冷却機によって冷却された凝縮器を用いて、光反応装置を組み立てた。400 Wの中圧水銀灯を光源として使用した。反応容器はキャビネット中に据えた。ランプを点灯させた(冷却機温度は、反応器に存在する水が(出口の流れに取り付けた熱電対によって観察して)20℃~25℃の間に保たれるように設定した)。18時間、反応をさせておいた。固体を濾別し、ヘキサンで洗浄し、2.2 gの物質が回収されただけであった。濾液をトルエンで希釈し、硫酸ナトリウム溶液で洗浄した。水層をトルエンで逆抽出し、有機層を硫酸マグネシウム上で乾燥させ、ろ過し、溶媒を蒸発させた。物質をトルエンに溶かし、亜硫酸ナトリウム溶液を添加し、撹拌した。層を分離し、水層をトルエンで抽出し、一緒にした有機層を硫酸マグネシウム上で乾燥させ、ろ過し、溶媒を蒸発させた。残留物を0から100%の酢酸エチル/ヘキサンで溶離させるカラムクロマトグラフィーによって精製した。8.8 gの物質を得た(72%)。
2,11-ジメトキシトリフェニレン(8.8 g, 30.5 mmol)とピリジン塩酸塩(31.73 g, 274.6 mmol)の混合物を220℃に2時間加熱した。混合物を冷やし、水を添加した。得られた固体を濾別し、水で洗い、高真空下で乾燥させた。7.45 g(94%)の所望する生成物が得られた。
100 mLのジクロロメタン及び13 mLのピリジンにトリフェニレン-2,11-ジオール(7.45 g, 28.62 mmol)を添加し、その溶液を氷塩浴中で冷やした。その溶液に窒素下で、70 mLのジクロロメタン中のトリフルオロメタンスルホン酸無水物(19 mL, 114.49 mmol)を滴下して添加した。反応を2時間進行させ、メタノール及び水を添加することによって失活させ、次にジクロロメタンで希釈した。黄褐色固体を濾別し、ジクロロメタン及び水で洗った。濾液の層を分離し、水層をジクロロメタンで抽出した。有機抽出液を硫酸マグネシウム上で乾燥させ、ろ過し、溶媒を蒸発させて茶色固体を得た。この茶色固体を0から100%ジクロロメタン/ヘキサンで溶離するカラムクロマトグラフィーによって精製した。1.8 gの所望の生成物が得られた。上記の後処理でろ過した黄褐色固体は、170℃における昇華とそれに続く300 mLの沸騰トルエンからの2回の再結晶によって精製した。9.6 gの所望の物質が得られ、合計11.4 g(76%)だった。
トリフェニレン-2,11-ジリルビス(トリフルオロメタンスルホネート)(3.0 g, 5.72 mmol)、3-ビフェニルボロン酸(2.72 g, 13.73 mmol)、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(188 mg, 0.458 mmol)、リン酸三カリウム(7.21 g, 34.32 mmol)、トルエン(120 mL)、及び水(50 mL)の混合物を調製した。30分間その溶液中に直接窒素をバブリングさせた。次に、トリス(ジベンジリデンアセトン)ジパラジウム(0)(105 mg, 0.114 mmol)を添加し、反応混合物を夜通し窒素下で加熱し還流させた。反応混合物を冷やし、固体を濾別し、水及びメタノールで洗浄した。固体を沸騰トルエンに溶かし、硫酸マグネシウムを通してろ過した。後処理中に濾液から物質が分離した。一緒にした物質を、0から50%ジクロロメタン/ヘキサンで溶離するカラムクロマトグラフィー、昇華、20から30%ジクロロメタン/ヘキサンで溶離するカラムクロマトグラフィー、ジクロロメタン/ヘキサンからの再結晶、及び270℃での昇華によって精製した。1.5 g(50%)の純粋な生成物が得られた。
4-フェニル-1,2-ジクロロベンゼン
4-フェニル-1,2-ジクロロベンゼン(6.0 g, 26.9 mmol)、4-ビフェニルボロン酸(13.3 g, 67.2 mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(739 mg, 0.807 mmol)、フッ化カリウム(6.95 g, 120.0 mmol)、及び150 mLのTHFの混合物を調製した。この混合物を撹拌しながら、15分間それを通して窒素をバブリングさせた。次に、トリ-t-ブチルホスフィン(トルエン中1M, 1.6 mL, 1.614 mmol)を添加し、混合物を夜通し窒素下で還流させた。反応物を室温まで冷やし、セライトを通してろ過した。このセライトをジクロロメタンで洗い、濾液から溶媒を蒸発させた。残留物をジクロロメタンに溶かし、不溶性の灰白色固体を濾別した。濾液を、ジクロロメタン/ヘキサンで溶離するカラムクロマトグラフィーによって精製して、11.4 g(92%)の白色固体を得た。
150 mLのジクロロメタン中の4-フェニル-1,2-(4’-ビフェニル)ベンゼン(5 g, 10.90 mmol)の溶液を調製し、窒素下でドライアイス-アセトン浴中で冷やした。この溶液に、125 mLのジクロロメタン中の[ビス(トリフルオロアセトキシ)ヨード]ベンゼン(11.7 g, 27.26 mmol)及びボロントリフルオライド・ジエチルエーテル(4.1 mL, 32.7 mmol)の溶液を滴下して添加した。反応物を2時間、ドライアイス-アセトン浴中で撹拌し、次に、氷浴を使用して0℃まで温めた。反応をメタノール及び亜硫酸ナトリウム水溶液で失活させ、ジクロロメタンで希釈した。層を分離し、水層をジクロロメタンで抽出した。有機層を硫酸マグネシウム上で乾燥させ、ろ過し、残留物になるまで溶媒を蒸発させ、残留物をジクロロメタンに溶かした。不溶性の灰色固体を濾別した。濾液を溶媒蒸発させ、ジクロロメタン/ヘキサンで溶離させるカラムクロマトグラフィーによって精製した。生成物をキシレンから再結晶し、次に250℃で昇華させた。この物質を190℃で4日間昇華させて不純物を除去し、次に3:1のヘキサン:ジクロロメタンで溶離するカラムクロマトグラフィーによって精製して色を除いた。最後に、物質を230℃で昇華させて0.98 g(20%)の白色固体を得た。
1,2-(4’-ビフェニル)ベンゼン
110 mLのジクロロメタン中の1,2-(4’-ビフェニル)ベンゼン(4.44 g, 11.61 mmol)の溶液を調製し、窒素下でドライアイス-アセトン浴中で冷やした。この溶液に、100 mLのジクロロメタン中の[ビス(トリフルオロアセトキシ)ヨード]ベンゼン(12.73 g, 29.6 mmol)とボロントリフルオライド・ジエチルエーテル(4.4 mL, 34.83 mmol)の溶液を滴下して添加した。この反応混合物を2時間、ドライアイス-アセトン浴中で撹拌し、次に氷塩浴を使用して0℃まで温めた。反応をメタノール及び亜硫酸ナトリウム水溶液で失活させ、ジクロロメタンで希釈した。エマルションが得られた。この混合物を次にセライトを通してろ過した。層を分離し、水層をジクロロメタンで抽出した。有機層を食塩水で洗い、硫酸マグネシウム上で乾燥させ、ろ過し、溶媒を蒸発させて残留物を得た。この残留物をジクロロメタン/ヘキサンで2回溶離するカラムクロマトグラフィーと、続いての210℃での昇華によって精製した。0.51 g(12%)の白色固体が得られた。
高真空熱蒸発(vacuum thermal evaporation; VTE)を用いて、1200Å厚さのITO上にデバイス1~9を作製した。全てのデバイスは以下のデバイス構造及び層厚さを用いて作製した。ITO/HIL(100Å)/HTL(300Å)/EML(300Å)/ETL2(50Å)/ETL1(450Å)/LiF/Al。これらの層は以下のように定義される。HILは正孔注入層であり、HTLは正孔輸送層であり、EMLはドープされた発光層であり、ETL2はエンハンスメント層であり、ETLは電子輸送層である。全てのデバイスは、ドーパント1を含むHIL、NPDのHTL、Alq3のETLを用いて作製した。EMLは、緑色発光ドーパント1で10質量%ドープされた様々な単一トリフェニレンホストを含む。用いたBLは、HPT又はトリフェニレンを有するホストのいずれかである。10Å厚さのLiFとそれに続く1000Å厚さのAl層をカソードとして用いた。全てのデバイスは40 mA/cm2の一定電流密度において寿命試験を行った。このVTEデバイスの特性を表1及び図3~8に示す。
ドーパント1及びHPTは以下の構造を有する。
デバイス10~15は以下のようにして溶液加工を用いて作製した。正孔注入層を、シクロヘキサノン中のHIL及びドーパントであるトリチルテトラキス(ペンタフルオロフェニル)ボレート(CD1)の0.25質量%溶液により、4000rpmで30秒間スピンコーティングした。その被膜を250℃で30分間焼成した。正孔輸送層については、トルエン中のN4,N4’-ジ(ナフタレン-1-イル)-N4,N4’-ビス(4-ビニルフェニル)ビフェニル-4,4’-ジアミンの1.0質量%溶液をその正孔注入層の上に、4000rpmで30秒間スピンコーティングした。被膜を次に200℃で30分間、グローブボックス中のホットプレート上で焼成した。被膜は焼成後、不溶性になった。室温に冷却後、その正孔輸送層上に1000rpmで30秒間、0.75質量%のホスト及びドーパント2(ホストとドーパントの比は88:12)の溶液をスピンコーティングすることによって発光層を堆積させた。この発光層を次に100℃で1時間焼成した。2,3,6,7,10,11-ヘキサフェニルトリフェニレン(HPT)の5 nm厚さの層とAlq3の50 nm厚さの層を次に真空熱蒸発によって堆積させ、次にLiF/Alカソードを堆積させた。
Claims (6)
- アノード、カソード、及び前記アノードと前記カソードとの間に配置された有機層を含む有機発光デバイスの有機層であって、
前記有機層が、発光ドーパントとともに、下記サブ構造F:
を有する化合物をホストとして含む発光層である、有機発光デバイスの有機層。 - 請求項1に記載の有機層を形成している、サブ構造Fを有する化合物及び発光ドーパントを含む組成物。
- アノード、カソード、及び前記アノードと前記カソードとの間に配置された有機層を含む有機発光デバイスの有機層であって、
前記有機層が、発光ドーパントとともに、下記サブ構造F:
を有する化合物をホストとして含む発光層である、有機発光デバイスの有機層。 - 請求項3に記載の有機層を形成している、サブ構造Fを有する化合物及び発光ドーパントを含む組成物。
- アノード、カソード、及び前記アノードと前記カソードとの間に配置された有機層を含む有機発光デバイスの有機層であって、
前記有機層が、発光ドーパントとともに、下記サブ構造G:
を有する化合物をホストとして含む発光層である、有機発光デバイスの有機層。 - 請求項5に記載の有機層を形成している、サブ構造Gを有する化合物及び発光ドーパントを含む組成物。
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