CN112912370B - Polycyclic compound and organic light-emitting element including the same - Google Patents
Polycyclic compound and organic light-emitting element including the same Download PDFInfo
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- CN112912370B CN112912370B CN202080005755.4A CN202080005755A CN112912370B CN 112912370 B CN112912370 B CN 112912370B CN 202080005755 A CN202080005755 A CN 202080005755A CN 112912370 B CN112912370 B CN 112912370B
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- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 239000012044 organic layer Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 239000002019 doping agent Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 238000004608 ZINDO calculation Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QTNASVGRWVSNNH-UHFFFAOYSA-N [Ir].C1(=CC=CC=C1)N1CC=CC2=CC=CC=C12.C1(=CC=CC=C1)N1CC=CC2=CC=CC=C12 Chemical compound [Ir].C1(=CC=CC=C1)N1CC=CC2=CC=CC=C12.C1(=CC=CC=C1)N1CC=CC2=CC=CC=C12 QTNASVGRWVSNNH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000005428 anthryl 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 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
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- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 238000005314 correlation function Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 238000007429 general method Methods 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
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- SHNBXKOUKNSCSQ-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 SHNBXKOUKNSCSQ-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- YTIFDAAZLZVHIX-UHFFFAOYSA-N naphtho[1,2-g][1]benzofuran Chemical compound C1=CC=C2C3=CC=C4C=COC4=C3C=CC2=C1 YTIFDAAZLZVHIX-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
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Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present specification claims priority from korean patent application No. 10-2019-0013525, filed to the korean patent office on 1-2-2019, the entire contents of which are included in the present specification.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of the organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and excitons (exciton) are formed when the injected holes and electrons meet each other, and light is emitted when the excitons transition to the ground state again.
The substances used in the organic light emitting device are mostly pure organic substances or complex compounds of organic substances and metals constituting complexes. The materials used for the above-mentioned organic light emitting device can be classified into a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like according to the purpose. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. As the light-emitting layer substance, a substance having both p-type property and n-type property, that is, a substance having a stable form in both of an oxidized state and a reduced state is preferable, and when an exciton is formed, it is preferable to be converted into a substance having high light emission efficiency.
In order to fully develop the excellent characteristics of the organic light-emitting device, development of a substance constituting an organic layer in the device is continuously demanded.
(Patent document 1) Korean patent laid-open No. 10-2016-034804
Disclosure of Invention
Technical problem
In the present specification, a compound and an organic light emitting device including the same are described.
Solution to the problem
An embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
X is O, S or Si, and the silicon dioxide is selected from the group consisting of,
Ar 1 to Ar 4 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with an adjacent group to form a substituted or unsubstituted carbazole,
R 1 to R 8 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and 1 or more of R 1 to R 8 are deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode, and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer contain a compound represented by the chemical formula 1.
Effects of the invention
The compound described in this specification is not only easy to manufacture, but also when included as a material of an organic material layer of an organic light-emitting device, an organic light-emitting device having a low driving voltage, excellent efficiency and lifetime characteristics can be obtained.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
1: Substrate board
2: Anode
3: Light-emitting layer
4: Cathode electrode
5: Hole injection layer
6: Hole transport layer
7: Light-emitting layer
8: Electron transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the following chemical formula 1. The compound represented by the following chemical formula 1 is not only easy to manufacture compared with a core structure having an amine group substituted at a different position, but also has 2 amine groups bonded at specific positions of a five-ring condensed heterocyclic ring, and thus, when applied to an organic light-emitting device, a device having excellent device efficiency, light-emitting efficiency and lifetime characteristics can be obtained.
In addition, according to an embodiment of the present specification, when the compound represented by the following chemical formula 1 is applied as a dopant of a light emitting layer in an organic light emitting device, energy transfer (ENERGY TRANSFER) with a host is easy, and thus a device having high light emitting efficiency and long life characteristics can be obtained. In the following chemical formula 1, a compound containing 1 amine group or no amine group is not suitable for use as a dopant of a light emitting layer not only in light emission wavelength but also has very low light emission efficiency when applied to a device, and the compound of the following chemical formula 1 has high quantum efficiency (QE, quantum Efficiency) compared with a compound having a different condensed position of a benzene ring to which an amine group is bonded in chemical formula 1, and thus has an advantage of exhibiting high light emission efficiency when applied to a device.
In addition, the compound represented by the following chemical formula 1 contains 1 or more substituents other than hydrogen in the condensed heterocyclic ring of the pentacyclic ring, and is electronically stable, whereby a device having excellent lifetime characteristics can be obtained when applied to a device, and when applied as a dopant for a light-emitting layer, wavelength can be easily adjusted, thereby exhibiting excellent light-emitting efficiency and hue.
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
X is O, S or Si, and the silicon dioxide is selected from the group consisting of,
Ar 1 to Ar 4 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with an adjacent group to form a substituted or unsubstituted carbazole,
R 1 to R 8 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and 1 or more of R 1 to R 8 are deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano (-CN), nitro, hydroxy, silyl, boron group, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, cycloalkyl, aryl, and heterocyclic group, or a substituent bonded with 2 or more substituents among the above exemplified substituents, or does not have any substituent. The "substituent formed by connecting 2 or more substituents" may be a phenylnaphthyl group. That is, phenyl naphthyl may be aryl, or may be interpreted as a phenyl group substituted on the naphthyl.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by a chemical formula of-SiY aYbYc, and the above Y a、Yb and Y c may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be represented BY the chemical formula of-BY dYe, and the above Y d and Y e may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include, but are not limited to, dimethylboronyl, diethylboronyl, t-butylmethylboronyl, diphenylboronyl, phenylboronyl, and the like.
In the present specification, the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms.
As specific examples of the above alkyl group, there are methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and the like, and the above alkyl group may be straight-chain or branched, and according to one example, propyl group includes n-propyl group and isopropyl group, and butyl group includes n-butyl group, isobutyl group and tert-butyl group.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl (adamantane,) And the like, but is not limited thereto.
In the present specification, the alkyl group of the alkoxy group may be applied to the above description regarding the alkyl group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl,Examples of the group include, but are not limited to, a fluorenyl group, a fluoranthenyl group, and a triphenylene group.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
In the case where the fluorenyl group is substituted, it may be that A spirofluorenyl group such as (spiroadamantane fluorene); /(I)(9, 9-Dimethylfluorenyl);(9, 9-Diphenylfluorenyl) and the like. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a ring group containing 1 or more hetero atoms of N, O, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, quinolyl, thienyl, dibenzothienyl, furyl, dibenzofuryl, naphthobenzofuryl, carbazolyl, benzocarbazolyl, naphthobenzothienyl, and the like.
In this specification, the heteroaryl group is not aromatic, and the above description about the heterocyclic group can be applied.
In the present specification, the hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, the description of the aryl group may be applied to the aromatic hydrocarbon ring except for the 2-valent group, and the description of the cycloalkyl group may be applied to the aliphatic hydrocarbon ring except for the 2-valent group.
According to an embodiment of the present disclosure, X is O, S or Si. When X is O, S or Si, the thermal stability is superior to that of a compound in which X is C, and thus sublimation purification and device evaporation are easy, and the lifetime characteristics of the device are improved.
According to an embodiment of the present specification, the above R 1 to R 8 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and 1 or more of R 1 to R 8 are deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to another embodiment, the above-mentioned R 1 to R 8 are the same or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and 1 or more of R 1 to R 8 are deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In another embodiment, R 1 to R 8 are the same or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and 1 or more of R 1 to R 8 are deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.
According to another embodiment, the above R 1 to R 8 are the same or different from each other, each is independently hydrogen, deuterium, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, or substituted or unsubstituted cyclohexyl, and 1 or more of R 1 to R 8 are deuterium, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, or substituted or unsubstituted cyclohexyl.
In another embodiment, R 1 to R 8 are the same or different from each other, each is independently hydrogen, deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl, and 1 or more of R 1 to R 8 are deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl.
According to an embodiment of the present specification, 1 or more of R 1 and R 6 are deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and the balance is hydrogen.
According to another embodiment, 1 or more of R 1 and R 6 are deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and the balance is hydrogen.
According to another embodiment, 1 or more of R 1 and R 6 are deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and the balance is hydrogen.
According to another embodiment, more than 1 of the above R 1 and R 6 are deuterium, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, or substituted or unsubstituted cyclohexyl, the remainder being hydrogen.
According to another embodiment, more than 1 of the above-mentioned R 1 and R 6 is deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl, the remainder being hydrogen.
In another embodiment, R 1 is deuterium, ethyl, isopropyl, t-butyl, cyclopentyl or cyclohexyl.
According to another embodiment, R 6 is deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl.
In another embodiment, R 1 and R 6 above are the same or different from each other, each independently deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl, or cyclohexyl.
According to an embodiment of the present specification, the above-mentioned Ar 1 to Ar 4 are the same as or different from each other, each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 40 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing O, S or N as a hetero atom, or a substituted or unsubstituted carbazole is formed by combining with an adjacent group.
In another embodiment, ar 1 to Ar 4 described above are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing O, S or N as a hetero atom, or a substituted or unsubstituted carbazole is formed by combining with an adjacent group.
In another embodiment, ar 1 to Ar 4 described above are the same or different from each other, and each independently is an alkyl group having 1 to 20 carbon atoms; aryl groups of 6 to 60 carbon atoms substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano groups, alkyl groups of 1 to 20 carbon atoms, trialkylsilyl groups of 3 to 20 carbon atoms, and cycloalkyl groups of 3 to 30 carbon atoms; or a heterocyclic group containing O, S or N as a hetero atom, which is substituted or unsubstituted with 1 or more substituents selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, having 2 to 60 carbon atoms, or a carbazole substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms is formed by bonding adjacent groups to each other.
According to another embodiment, the above-mentioned Ar 1 to Ar 4 are the same or different from each other, each is independently a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spiroadamantylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group, or 1 or more selected from Ar 1 and Ar 2, and Ar 3 and Ar 4 are combined with each other to form a substituted or unsubstituted carbazole. The above-mentioned "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a trialkylsilyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms.
In another embodiment, ar 1 to Ar 4 above are the same or different from each other, each independently is a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or the following chemical formula a, or is combined with each other to form a substituted or unsubstituted carbazole. The above-mentioned "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms.
[ Chemical formula A ]
In the above-mentioned chemical formula a,
R 30 is hydrogen, deuterium, a halogen group, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,
N1 is an integer of 0 to 7, and when n1 is 2 or more, 2 or more R 30 are the same or different from each other,
The position of the bond is indicated.
According to another embodiment, ar 1 to Ar 4 described above are the same or different from each other, each independently being ethyl; phenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; a terphenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; phenanthryl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; fluorenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; benzofluorenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; a spiroadamantylfluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; dibenzofuranyl substituted or unsubstituted with 1 or more substituents selected from methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; dibenzothienyl substituted with 1 or more substituents selected from methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; or a carbazolyl group substituted or unsubstituted with 1 or more substituents selected from methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl, or 1 or more substituents selected from Ar 1 and Ar 2, and Ar 3 and Ar 4 are bonded to each other to form a carbazole substituted or unsubstituted with butyl.
According to an embodiment of the present specification, the above Ar 1 to Ar 4 are the same as or different from each other, and are each independently selected from an alkyl group having 1 to 10 carbon atoms, and a structure described below, or are combined with each other with an adjacent group to form a substituted or unsubstituted carbazole.
In the above-described structure, the first and second heat exchangers,
W is O, S or NR 103,
R 101 to R 103 are identical to or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
The above structure may be substituted with 1 or more substituents selected from deuterium, halogen group, cyano group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, and substituted or unsubstituted aryl group,
In the above structure, the bonding position is indicated.
According to an embodiment of the present specification, the above structure may be further substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 20 carbon atoms, a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms.
According to another embodiment, the above structure may be further substituted with 1 or more substituents selected from deuterium, halogen group, cyano, trimethylsilyl, methyl, isopropyl, t-butyl, cyclopentyl and cyclohexyl.
According to an embodiment of the present specification, the above-mentioned R 101 to R 103 are the same or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In another embodiment, R 101 to R 103 are the same or different from each other and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, the above-mentioned R 101 to R 103 are the same or different from each other, and are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
In another embodiment, R 101 to R 103 described above are the same or different from each other, each independently hydrogen, deuterium, methyl, isopropyl, tert-butyl, or phenyl substituted or unsubstituted with tert-butyl.
According to an embodiment of the present specification, the above-mentioned-N (Ar 1)(Ar2) and-N (Ar 3)(Ar4) are the same or different from each other, and each is independently represented by the following chemical formula 1-A or 1-B.
[ Chemical formula 1-A ]
[ Chemical formula 1-B ]
In the above chemical formulas 1-a and 1-B,
R 11 and R 12 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R 20 to R 27 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
In the above structure, the bonding position is indicated.
According to an embodiment of the present specification, the above R 11 and R 12 are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 40 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing O, S or N as a hetero atom.
In another embodiment, R 11 and R 12 described above are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing O, S or N as a hetero atom.
In another embodiment, R 11 and R 12 are the same or different from each other, and each is independently an alkyl group having 1 to 20 carbon atoms; aryl groups of 3 to 60 carbon atoms substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano groups, alkyl groups of 1 to 20 carbon atoms, trialkylsilyl groups of 3 to 20 carbon atoms, and cycloalkyl groups of 3 to 30 carbon atoms; or a heterocyclic group containing O, S or N as a hetero atom, which is substituted or unsubstituted with 1 or more substituents selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, and which has 2 to 60 carbon atoms.
According to another embodiment, the above R 11 and R 12 are the same or different from each other and are each independently a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spiroadamantylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.
According to another embodiment, R 11 and R 12 above are the same or different from each other, each independently being ethyl; phenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; a terphenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; phenanthryl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; fluorenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; benzofluorenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen groups, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; a spiroadamantylfluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano, methyl, isopropyl, t-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; dibenzofuranyl substituted or unsubstituted with 1 or more substituents selected from methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; dibenzothienyl substituted with 1 or more substituents selected from methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; or a carbazolyl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of methyl, t-butyl, t-butylphenyl, cyclopentyl and cyclohexyl.
According to an embodiment of the present specification, the above-mentioned R 20 to R 27 are the same or different from each other, and each is independently hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
According to another embodiment, the above-mentioned R 20 to R 27 are identical to or different from each other, each independently hydrogen, or substituted or unsubstituted tert-butyl.
According to an embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.
[ Chemical formula 1-1]
[ Chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
X, R 1 to R 8, and Ar 1 to Ar 3 are as defined in the above chemical formula 1,
R 30 and R 30' are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
N1 and n1 'are each integers of 0 to 7, and when n1 and n1' are each 2 or more, the structures in brackets of 2 or more are the same or different from each other.
According to an embodiment of the present disclosure, R 30 and R 30' are hydrogen.
In one embodiment of the present specification, each of n1 and n1' is 0 or 1.
According to an embodiment of the present specification, the above-mentioned-N (Ar 1)(Ar2) and-N (Ar 3)(Ar4) are the same or different from each other, and each is independently represented by any one of the following structures.
In the above structure, the bonding position is indicated.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is represented by any one of the following compounds.
The core structure of the compound represented by chemical formula 1in the present specification can be manufactured as shown in the following reaction formulas 1 to 4, and amine groups can be bound to the following intermediates E-1 to E-4 by amination reaction known in the art. In addition, additional substituents may be incorporated using methods known in the art, and the type, position and number of substituents may be varied according to techniques known in the art.
< Reaction No. 1>
1)
The above intermediate A-1 (56.1 g,175 mmol) and 3-bromonaphthalene-2, 7-diol [3-bromona phthalene-2,7-diol ] (44 g,184 mmol), K 2CO3 (145 g, 1050mmol) were added to 1, 4-di-ethyleneAlkane/water (4:1) (1500 mL). After 2g of tetrakis (triphenylphosphine) palladium (TTP) was added under reflux stirring, the mixture was refluxed and stirred for 12 hours. At the end of the reaction, the temperature was lowered to room temperature, and then the organic layer was extracted with water and ethyl acetate and separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform to produce intermediate B-1. (43.2 g, yield 70%, MS: [ M+H ] + =353)
2)
After the above intermediate B-1 (43.5 g,135.6 mmol) and CH 3SO2 OH (60 mL) were added, the mixture was stirred for 5 hours. After cooling to room temperature, the reaction product was poured into water, the resulting solid was filtered, and the resulting solid was recrystallized from chloroform and ethanol to produce the above intermediate C-1. (36.3 g, 88% yield, MS: [ M+H ] + =335)
3)
The intermediate C-1 (36.3 g,108 mmol) and isopropylboric acid [ isopropylboronicacid ] (10.5 g,119 mmol), K 2CO3 (74.6 g,540 mmol) were added to 1, 4-bis (Alkane/water (4:1) (1500 mL). 2g of tetrakis (triphenylphosphine) palladium (TTP) and 2g of DPPF (1, 1 '-bis (diphenylphosphine) ferrocene [1,1' -Ferrocendiylbis (diphenylp hosphine) ]) were introduced under reflux and stirred, and then refluxed and stirred for 12 hours. At the end of the reaction, after the temperature was lowered to normal temperature, extraction was performed with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform to produce intermediate D-1. (19.6 g, 53% yield, MS: [ M+H ] + =343)
4)
The intermediate D-1 (19.6 g,57.3 mmol) was added to tetrahydrofuran (1000 mL), and after stirring for 1 hour, K 2CO3 (23.7 g,172 mmol) was added after 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride [1, 2,3, 4-nonafluorobutane-1-sulfonyl fluoride ] (52 g,172 mmol), stirring was further carried out for 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, and the organic layer was extracted and separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol, thereby producing the above intermediate E-1. (42.6 g, yield 85%, MS: [ M+H ] + =915)
< Reaction No. 2>
1)
The above-mentioned compound A-1 (56.1 g,175 mmol) and 3-bromonaphthalene-2, 7-diol [3-bromona phthalene-2,7-diol ] (44 g,184 mmol), K 2CO3 (145 g,1050 mmol) were added to 1, 4-di-ethyleneAlkane/water (4:1) (1500 mL). After 2g of tetrakis (triphenylphosphine) palladium (TTP) was added under reflux stirring, the mixture was refluxed and stirred for 12 hours. At the end of the reaction, after the temperature was lowered to normal temperature, extraction was performed with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform to produce intermediate B-2. (43.2 g, yield 70%, MS: [ M+H ] + =353)
2)
After the above intermediate B-2 (48.1 g,124.2 mmol) and CH 3SO2 OH (70 mL) were added, the mixture was stirred for 5 hours. After cooling to room temperature, the reaction product was poured into water, the resulting solid was filtered, and the resulting solid was recrystallized from chloroform and ethanol, to thereby produce the above intermediate C-2. (37.1 g, 81% yield, MS: [ M+H ] + =370)
3)
The intermediate C-2 (37.1 g,100.6 mmol) and cyclohexylboric acid [ cyclohexylboronic acid ] (28.3 g,221.3 mmol) and K 2CO3 (111.2 g,804.8 mmol) were added to 1, 4-bis-Alkane/water (4:1) (1500 mL). 4g of tetrakis (triphenylphosphine) palladium (TTP) and 4g of DPPF (1, 1 '-bis (diphenylphosphine) ferrocene [1,1' -Ferrocendiylbis (diphenylphosphine) ]) were introduced under reflux and stirred, and then refluxed and stirred for 12 hours. At the end of the reaction, after the temperature was lowered to normal temperature, extraction was performed with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform to produce intermediate D-2. (25.7 g, yield 55%, MS: [ M+H ] + =465)
4)
The intermediate D-2 (25.7 g,55.3 mmol) was poured into tetrahydrofuran (1000 mL), and after stirring for 1 hour, K 2CO3 (23 g,165.9 mmol) was added after 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride [1, 2,3, 4-nonafluorobutane-1-sulfonyl fluoride ] (52 g,172 mmol), stirring was further carried out for 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, extraction was performed, and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol, thereby producing the above intermediate E-2. (49.6 g, yield 90%, MS: [ M+H ] + =997)
< Reaction No. 3>
1)
The above intermediate C-2 (37.1 g,100.6 mmol) and 2,4,4,5,5-pentamethyl-1, 3, 2-dioxaborolane [2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane](31.4g,221.3mmol)、K2CO3(111.2g,804.8mmol) were charged to 1, 4-dioAlkane/water (4:1) (1500 mL). 4g of tetrakis (triphenylphosphine) palladium (TTP) and 4g of DPPF (1, 1 '-bis (diphenylphosphine) ferrocene [1,1' -Ferrocendiylbis (diphenylphosphine) ]) were introduced under reflux and stirred, and then refluxed and stirred for 12 hours. At the end of the reaction, after the temperature was lowered to normal temperature, extraction was performed with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform to produce intermediate D-3. (15.8 g, yield 48%, MS: [ M+H ] + =329)
2)
The intermediate D-3 (18.2 g,55.3 mmol) was added to tetrahydrofuran (1000 mL), and after stirring for 1 hour, K 2CO3 (23 g,165.9 mmol) was added after 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride [1, 2,3, 4-nonafluorobutane-1-sulfonyl fluoride ] (52 g,172 mmol), stirring was further carried out for 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, extraction was performed, and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol, thereby producing the above intermediate E-3. (44.9 g, 91% yield, MS: [ M+H ] + =893)
< Reaction 4>
1)
The above intermediate C-2 (37.1 g,100.6 mmol) and 2-isopropyl-4, 5-tetramethyl-1, 3, 2-dioxaborolane [2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane](37.6g,221.3mmol)、K2CO3(111.2g,804.8mmol) were added to 1, 4-dioAlkane/water (4:1) (1500 mL). 4g of tetrakis (triphenylphosphine) palladium (TTP) and 4g of DPPF (1, 1 '-bis (diphenylphosphine) ferrocene [1,1' -Ferrocendiylbis (diphenylphosphi ne) ]) were introduced under reflux and stirred, and then refluxed and stirred for 12 hours. At the end of the reaction, after the temperature was lowered to normal temperature, extraction was performed with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform to produce intermediate D-4. (19.3 g, yield 50%, MS: [ M+H ] + =385)
2)
The intermediate D-4 (21.3 g,55.3 mmol) was added to tetrahydrofuran (1000 mL), and after stirring for 1 hour, K 2CO3 (23 g,165.9 mmol) was added after 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride [1, 2,3, 4-nonafluorobutane-1-sulfonyl fluoride ] (52 g,172 mmol), stirring was further carried out for 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, extraction was performed, and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol, thereby producing the above intermediate E-4. (44.6 g, yield 85%, MS: [ M+H ] + =949)
By introducing various substituents into the compound represented by the above chemical formula 1, compounds having various energy bandgaps can be synthesized. In addition, in this specification, by introducing various substituents into the core structure of the structure described above, the HOMO (highest occupied molecular orbital ) and LUMO (lowest unoccupied molecular orbital, lowest unoccupied molecular orbital) energy levels of the compound can also be adjusted.
In the present specification, "energy level" refers to the amount of energy. Therefore, even when the energy level is expressed from the vacuum level to the negative (-) direction, the energy level is interpreted to mean the absolute value of the energy value. For example, HOMO (highest occupied molecular orbital) energy level refers to the distance from the vacuum energy level to the highest occupied molecular orbital. In addition, LUMO (lowest unoccupied molecular orbital) energy level refers to a distance from a vacuum energy level to the lowest unoccupied molecular orbital.
According to an embodiment of the present specification, the compound represented by chemical formula 1 above may have a band gap energy (band GAP ENERGY) of 2.6eV to 2.9 eV. When the above compound is used as a blue dopant in a light-emitting layer of an organic light-emitting device, a device having high efficiency can be obtained by having an appropriate emission wavelength value. The band gap energy can be measured by the method of experimental example 1 described later.
Specifically, the band gap energy (band GAP ENERGY) value refers to the difference between the HOMO (highest occupied molecular orbital) energy level and the LUMO (lowest unoccupied molecular orbital) energy level, which can be measured as follows.
To determine the molecular structure of a chemical, the structure of the input is optimized using the density functional method (density functional theory, DFT). For DFT calculation, the BPW91 algorithm (beck exchange function and Perdew correlation function), beck exchange AND PERDEW correlation-correlation functional) and DNP (binary basis set of polarization functions, double numerical basis set including polarization functional) basis set (basis set) are used. The BPW91 algorithm is disclosed in papers "A.D.Becke, phys.Rev.A,38,3098 (1988)" and "j.p. perdew and Y.Wang, phys.Rev.B,45,13244 (1992)", and the DNP basis set is disclosed in papers "B.Delley, J.Chem.Phys.,92,508 (1990)".
To perform the calculation with the density functional method, a "DMol3" package (package) from Biovia can be used. When the optimal molecular structure is determined by the method given above, the electron-occupiable energy level can be obtained as a result. The HOMO energy is the orbital energy of the highest energy level among the electron-filled molecular orbitals when the energy in the neutral state is obtained, and the LUMO energy corresponds to the orbital energy of the lowest energy level among the electron-unfilled molecular orbitals.
* HOMO/LUMO calculation
Experimentally, the HOMO level is measured by using an IP (ionization potential ) value (formula-1 below) measured by using a UPS (ultraviolet electron spectrum, ultraviolet photoemission spectroscopy) or the like, and the LUMO level is generally obtained by subtracting an Optical Gap (Optical Gap) from the HOMO level (formula-2 below).
[ 1]
Homo=ip (ionization potential)
[ 2]
Lumo=ip-optical energy gap
The values actually measured in the corresponding experiments are provided together with HOMO and LUMO in the theoretical neutral state and calculated by the following two methods.
Method 1) method using IP and optical energy gap
According to the calculation method in the experiment, the IP and optical energy gap of the X molecule were obtained by using the following formulas-3 and-4.
[ 3]
IP (ionization potential) =e x+ Cations (cationic) -Ex Neutral
[ 4]
Optical gap=e S1 S0-ES0 S0
In the above-mentioned formula-3, the catalyst,Refers to an energy of charge (charge) of 0, X +, or X - in a structure in which geometry is optimized to be cationic (cation), anionic (anion), or neutral (neutral). That is, the electron affinity refers to the difference between the most stable energy of the neutral structure and the most stable energy of the anion, and may refer to the energy released when one electron is added in the neutral state.
In the above formula-4, S0 means a singlet state of the ground state (groudstate), S1 means a singlet state of the first excited state (excit edstate), E S1 S0 means a difference between the singlet energy of the ground state and the singlet energy of the first excited state, and E S0 S0 means an energy difference inside the singlet state of the ground state. At this time, E S0 S0 refers to an energy difference caused by a geometry change inside the singlet state of the ground state. Further, assuming that the structural changes of S0 and S1 are not large, the energy absorbed (absorption) is similar to the fluorescence (fluorescence) value. Thus, the optical bandgap corresponds to the S0-S1 bandgap (gap). The energy of the ground state and the excited state is based on a value calculated by using a density functional.
Method 2) method of utilizing Solid state IP and optical energy gap
Since the layer is formed in a solid state (solid state) other than a single molecule, the effect at that time is corrected in consideration of the molecular shape and the like as shown in the following formula-5, and a HOMO calculated (HOMO calc) value can be obtained, and the LUMO energy level can be obtained by substituting this value into the IP value of the above formula-2. But cannot calculate the transition metal.
[ 5]
HOMO calculation = IP + [ delta ] (solid/molecule)
In the above formula-5, Δ (solid/molecule) means the difference between energies in a single-molecule state (Molecular state) and a solid state (solid state), and may affect the Asphericity (ASPHERICITY), radius of gyration (Radius of gyration), molecular weight (Molecular weight), and the like.
An organic light-emitting device according to the present specification, characterized by comprising: a first electrode, a second electrode, and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer contain a compound represented by the above-mentioned chemical formula 1.
The organic light-emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the compound represented by chemical formula 1.
The organic layer containing the compound represented by the above chemical formula 1 may be formed not only by a vacuum evaporation method but also by a solution coating method in manufacturing an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a layer that performs hole transport and hole injection simultaneously, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron transport and electron injection simultaneously, and the like as the organic layer. The structure of the organic light emitting device is not limited thereto and may include a smaller or larger number of organic layers.
In the organic light emitting device of the present specification, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include a compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.
According to another embodiment, the organic layer includes a light emitting layer including a compound represented by the above chemical formula 1 as a dopant of the light emitting layer, and the maximum light emitting wavelength of the dopant is 430nm to 470nm. The compound of the present invention contains 2 amine groups and thus has a maximum light emission wavelength in the above-mentioned range, but the compound containing 1 amine group has a maximum light emission wavelength in the range of about 410nm to 430 nm.
The light-emitting layer may further include a host having a maximum light-emitting wavelength of 400nm to 440nm, and the compound of the present invention including 2 amine groups may have excellent efficiency in that it is easy to transfer energy (ENERGY TRANSFER) in relation to the host, but the compound including 1 amine group may not smoothly transfer energy in relation to the host, and thus the efficiency of the device may be reduced. The maximum emission wavelength may be measured at normal temperature after diluting the compound to be measured with 1X10 -5 M/L in toluene. The maximum luminescence peak of the above-mentioned compound was measured by using FP-8600 from JASCO corporation, and the luminescence spectrum at the excitation wavelength of 300nm was 430nm to 470nm, and HPLC-grade anhydrous toluene (HPLC GRADE anhydrous Toluene) was used as a solvent.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is included as a blue dopant in a light emitting layer of an organic light emitting device.
According to another embodiment, the compound represented by the above chemical formula 1 is contained in a light emitting layer of an organic light emitting device as a fluorescent dopant for a thermally activated delayed Fluorescence (TADF: THERMALLY ACTIVATED DELAYED Fluorescence) device. In this case, the compound is thermally activated in the light-emitting layer to delay fluorescence emission. The thermally activated delayed fluorescence emission means that transition between opposite systems is induced from a triplet excited state (triplet excited state) to a singlet excited state (singlet excited state), and excitons in the singlet excited state move to a ground state to cause fluorescence emission, whereby a highly efficient organic light emitting device can be obtained.
According to an embodiment of the present invention, the dopant including the compound represented by chemical formula 1 as a light-emitting layer may include a host such as an anthracene compound having the following structure, but is not limited thereto.
In another embodiment, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a dopant of the light emitting layer, and further including a fluorescent host or a phosphorescent host, and may include other organic compounds, metals, or metal compounds as dopants.
As another example, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a dopant of the light emitting layer, and further including a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.
According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the compound represented by chemical formula 1 as a host of the light emitting layer.
As another example, the organic layer includes a light emitting layer including the compound represented by the chemical formula 1 as a host of the light emitting layer, and may further include a dopant.
The light emitting layer includes a host and a dopant, and the content of the dopant may be 1 to 20 parts by weight, more preferably 1 to 5 parts by weight, with respect to 100 parts by weight of the host.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
For example, the above-described organic light emitting device may have a laminated structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(12) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer 3.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer 5, hole transport layer 6, light emitting layer 7, and electron transport layer 8.
For example, the organic light emitting device according to the present specification may be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition: physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance usable as a cathode is vapor deposited on the organic layer. In addition to this method, an organic electronic device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, a hole suppression layer, or the like, but the organic layer is not limited to this and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
Each layer constituting the organic light emitting device described below may be formed of 1 layer or 2 layers or more, and the layers of 2 layers or more may be formed of the same substance or may be formed of substances different from each other.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; a multilayer structure such as LiF/Al or LiO 2/Al, but not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
An electron-suppressing layer may be provided between the hole-transporting layer and the light-emitting layer. The electron suppression layer may be formed using materials known in the art.
The light-emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds) Pyrimidine derivatives, and the like, but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphor such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium, iridium bis (1-phenylisoquinoline) acetylacetonate), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, iridium bis (1-phenylquinoline) acetylacetonate), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or a phosphor such as Alq 3 (tris (8-hydroxyquinolino) aluminum, tris (8-hydroxyquinoline) aluminum) may be used, but is not limited thereto. When the light-emitting layer emits green light, a phosphorescent substance such as Ir (ppy) 3 (fac tris (2-PHENYLPYRIDINE) irium, planar tris (2-phenylpyridine) iridium) or a fluorescent substance such as Alq 3 (tris (8-hydroxyquinolino) aluminum, tris (8-hydroxyquinoline) aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4, 6-F 2ppy)2 Irpic), or a fluorescent material such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymer, PPV-based polymer may be used as the light-emitting dopant, but is not limited thereto.
A hole-suppressing layer may be provided between the electron-transporting layer and the light-emitting layer, and materials known in the art may be used.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting material is a material that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is suitable for a material having high mobility of electrons. Specific examples include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, and the like.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
Synthesis example
Synthesis example 1.
Intermediate E-3 (13.4 g,15.0 mmol) above and intermediate 1 (6.8 g,30.1 mmol) above were charged to xylene (200 mL). NatBuO (4.3 g) of bis (tri-t-butylphosphine) palladium [ BTP ] (0.2 g) was added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 3 times from ethyl acetate to produce the above compound 1. (4.7 g, yield 42%, MS: [ M+H ] + =744)
Synthesis example 2.
Intermediate E-3 (13.4 g,15.0 mmol) above and intermediate 2 (8.5 g,30.1 mmol) above were charged to xylene (200 mL). NatBuO (4.3 g) and BTP (0.2 g) were charged, and then stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 3 times from ethyl acetate to prepare the above compound 2. (6.4 g, yield 50%, MS: [ M+H ] + =856)
Synthesis example 3.
Intermediate E-4 (14.2 g,15.0 mmol) above and intermediate 3 (8.6 g,30.1 mmol) above were charged to xylene (200 mL). NatBuO (4.3 g) and BTP (0.2 g) were charged, and then stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 3 times from ethyl acetate to prepare the above-mentioned compound 3. (7.0 g, 51% yield, MS: [ M+H ] + =920)
Synthesis example 4.
Intermediate E-3 (13.4 g,15.0 mmol) above and intermediate 4 (8.7 g,30.1 mmol) above were charged to xylene (200 mL). NatBuO (4.3 g) and BTP (0.2 g) were charged, and then stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 3 times from ethyl acetate to prepare the above-mentioned compound 4. (7.2 g, yield 55%, MS: [ M+H ] + =874)
Synthesis example 5.
Intermediate E-1 (15.0 g,17.2 mmol) above and intermediate 5 (6.4 g,34.3 mmol) above were charged to xylene (200 mL). NatBuO (5.0 g) and BTP (0.2 g) were charged, and then stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 3 times from ethyl acetate to prepare the above-mentioned compound 5. (5.9 g, yield 50%, MS: [ M+H ] + =681)
Synthesis example 6.
Intermediate E-2 (15.0 g,15.0 mmol) and intermediate 6 (5.8 g,30.1 mmol) were added to xylene (200 mL). NatBuO (4.3 g) and BTP (0.2 g) were charged, and then stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized 3 times from ethyl acetate to prepare the above-mentioned compound 6. (7.1 g, 58% yield, MS: [ M+H ] + =818)
In the above synthesis examples, the synthesis procedures of the compounds 1 to 6 are exemplified, but intermediates to which various types of substituents are bonded may be synthesized by reactions known in the art, or compounds other than the above compounds 1 to 6 may be synthesized using commercially available intermediates.
Experimental example 1]
Simulation result values of compound 1, compound 1-1, comparative compound 1 and comparative compound 2 measured using the apparatus and conditions described below are shown in table 4 below. Based on the results of table 4 below, it is predicted that the band gap energies (band GAP ENERGY) of compound 1 and compound 1-1 have values suitable for use as blue dopants for the light emitting layer, but the emission wavelength ranges of comparative compounds 1 and2 having band gap energies exceeding 2.9eV are unsuitable for use as blue dopants, and thus the light emitting efficiency will be very low.
DFT calculation (DFT calculation): BPW91/DND (DMol 3)
Geometric optimization (Geometry optimization): single point energy calculation (Single point energy calculation)
UV calculation (UV calculation): ZINDO (G03)
Band gap calculation (Band gap calculation): TD (G03)
Solid IP computation (Solid state IP calculation): QSPR (Aldriana, adriana)
TABLE 4
Experimental example 2
Example 1.
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was distilled water filtered twice using a Filter (Filter) manufactured by millbore co., ltd. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, the following HAT was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HT-A vacuum deposition/>, was performed as a hole transport layerThe following HT-B was vapor depositedAs a light-emitting layer, the following compound 1 as a dopant was doped with 4wt% in the following H-A as a host and was used as aVacuum evaporation was performed in thickness. Then, the following ET-A and the following Liq were vapor deposited at a ratio of 1:1On top of it, vapor depositionMagnesium (Mg) doped with 10wt% silver (Ag) to a thickness ofAluminum is formed in a thickness to form a cathode, thereby manufacturing an organic light emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedLiF maintenanceVapor deposition rate of aluminum maintenanceToIs a vapor deposition rate of (a).
Examples 2 to 21 and comparative examples 1 to 9
In example 1 above, an organic light-emitting device was manufactured in the same manner as in example 1, except that the compounds described in tables 1 to 3 below were used instead of H-a as the main body of the light-emitting layer, and the compounds described in tables 1 to 3 below were used instead of compound 1 as the dopant of the light-emitting layer.
For the organic light emitting devices of examples 1 to 21 and comparative examples 1 to 9 described above, the driving voltage and the light emitting efficiency were measured at a current density of 10mA/cm 2, and the time (LT 95) at which the initial luminance became 95% was measured at a current density of 20mA/cm 2. The results are shown in tables 1 to 3 below.
TABLE 1
TABLE 2
TABLE 3
Based on the above tables 1 to 3, it was confirmed that the driving voltages of the devices of examples 1 to 21 of the present application were low, and the efficiency and lifetime were very excellent, as compared with comparative examples 1 to 9.
Specifically, each of comparative examples 1 and 3 to 7 used a compound D-1, a compound D-3, a compound D-4, a compound D-5, or a compound D-6, in which pyrene, naphthobenzofuran, fluorene, dibenzofluorene, or dinaphthofuran was bonded between 2 amine groups, as a dopant of the light emitting layer, but it was confirmed that the performance was degraded compared to a device using the compound of the present application.
Comparative examples 2 and 8 used the compound D-2 having a binding site of an amine group different from that of the compound of the present application, and confirmed that the device performance was lowered, particularly, the device lifetime was very low, as compared with the device using the compound of the present application.
In comparative example 9, compound D-7 was used, and the compound D-7 was found to have the same bonding position between the core structure and the amine group as compared with the compound of the present application, but the dinaphthofuran as the core structure was not bonded with any substituent other than the amine group, and it was confirmed that the driving voltage was high and the efficiency and the lifetime were reduced as compared with the device using the compound of the present application.
Claims (7)
1. A compound represented by the following chemical formula 1:
Chemical formula 1
Wherein, in the chemical formula 1,
X is O or S, and the X is O or S,
Ar 1 to Ar 4 are the same or different from each other and are each independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, and a trialkylsilyl group having 3 to 20 carbon atoms, and
In R 1 to R 8, 1 or more of R 1 and R 6 are a linear or branched alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 30 carbon atoms, and the balance is hydrogen.
2. The compound according to claim 1, wherein the Ar 1 to Ar 4 are the same or different from each other and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a benzofluorenyl group, which is unsubstituted or substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, and a trialkylsilyl group having 3 to 20 carbon atoms.
3. The compound of claim 1, wherein Ar 1 to Ar 4 are the same or different from each other and are each independently selected from the following structures:
Wherein, in the structure, the first and second parts are arranged,
R 101 to R 102 are the same or different from each other and are each independently hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms,
The structure is optionally substituted with 1 or more substituents selected from deuterium, halogen group, cyano group, trialkylsilyl group of 3 to 20 carbon atoms, and straight or branched alkyl group of 1 to 20 carbon atoms,
Wherein in the structure described above, in the present invention,Indicating the location of the bond.
4. The compound of claim 1, wherein the-N (Ar 1)(Ar2) and-N (Ar 3)(Ar4) are the same or different from each other and are each independently represented by any one of the following structures:
Wherein in the structure described above, in the present invention, Indicating the location of the bond.
5. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following compounds:
6. An organic light emitting device, comprising: a first electrode, a second electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein the organic layers include a light-emitting layer containing the compound according to any one of claims 1 to 5 as a dopant of the light-emitting layer, and the maximum light-emitting wavelength of the dopant is 430nm to 470nm.
7. The organic light-emitting device of claim 6, wherein the light-emitting layer further comprises a host having a maximum light emission wavelength of 400nm to 440 nm.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104638202A (en) * | 2013-11-08 | 2015-05-20 | 北京鼎材科技有限公司 | Organic thin-film transistor and production method thereof |
| KR20170136980A (en) * | 2016-06-02 | 2017-12-12 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| CN108336239A (en) * | 2017-01-04 | 2018-07-27 | 株式会社Lg化学 | Organic illuminating element |
| CN108779072A (en) * | 2016-03-14 | 2018-11-09 | 株式会社Lg化学 | Heterocyclic compound and organic illuminating element comprising it |
| WO2018235953A1 (en) * | 2017-06-23 | 2018-12-27 | 出光興産株式会社 | Novel compound, material for organic electroluminescence element using same, organic electroluminescence element, and electronic device |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014104144A1 (en) * | 2012-12-26 | 2014-07-03 | 出光興産株式会社 | Oxygen-containing fused ring amine compound, sulphur-containing fused ring amine compound, and organic electroluminescent element |
| KR101864473B1 (en) | 2014-09-22 | 2018-06-04 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR102630643B1 (en) * | 2015-05-27 | 2024-01-31 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| KR20160141361A (en) * | 2015-05-27 | 2016-12-08 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| KR20170082459A (en) * | 2016-01-06 | 2017-07-14 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
-
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104638202A (en) * | 2013-11-08 | 2015-05-20 | 北京鼎材科技有限公司 | Organic thin-film transistor and production method thereof |
| CN108779072A (en) * | 2016-03-14 | 2018-11-09 | 株式会社Lg化学 | Heterocyclic compound and organic illuminating element comprising it |
| KR20170136980A (en) * | 2016-06-02 | 2017-12-12 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| CN108336239A (en) * | 2017-01-04 | 2018-07-27 | 株式会社Lg化学 | Organic illuminating element |
| WO2018235953A1 (en) * | 2017-06-23 | 2018-12-27 | 出光興産株式会社 | Novel compound, material for organic electroluminescence element using same, organic electroluminescence element, and electronic device |
Non-Patent Citations (3)
| Title |
|---|
| 徐峰等.聚芳醚非共轭性电致发光材料与器件.《发光学报》.2005,第26卷(第2期),第253-256页. * |
| 曲红梅等.二萘并噻咯的合成及性能.《物理化学学报》.2017,第33卷(第6期),第1253−1260页. * |
| 马良等.发光层厚度对红光磷光聚芴电致发光性能的影响.《闽江学院学报》.2010,第31卷(第2期),第100-103页. * |
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