JP2021524155A - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
- Publication number
- JP2021524155A JP2021524155A JP2020563926A JP2020563926A JP2021524155A JP 2021524155 A JP2021524155 A JP 2021524155A JP 2020563926 A JP2020563926 A JP 2020563926A JP 2020563926 A JP2020563926 A JP 2020563926A JP 2021524155 A JP2021524155 A JP 2021524155A
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- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- light emitting
- deuterium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 239000000126 substance Substances 0.000 claims abstract description 129
- 239000011368 organic material Substances 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 296
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 85
- 229910052805 deuterium Inorganic materials 0.000 claims description 78
- -1 phenylpyri Dinyl group Chemical group 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 238000002347 injection Methods 0.000 claims description 54
- 239000007924 injection Substances 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 2
- 230000032258 transport Effects 0.000 description 40
- 230000005525 hole transport Effects 0.000 description 34
- 238000000034 method Methods 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 125000004093 cyano group Chemical group *C#N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 230000002194 synthesizing effect Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000000151 deposition Methods 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 230000033228 biological regulation Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- BXGFEJRAJIFUSE-UHFFFAOYSA-N 2-[4-(4-bromonaphthalen-1-yl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=C(C2=CC=CC=C12)C1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 BXGFEJRAJIFUSE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 150000002469 indenes Chemical group 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical group C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- 0 **c1c(c(*)c(*)c(*)c2*)c2c(**)c2c1c(*)c(*)c(*)c2* Chemical compound **c1c(c(*)c(*)c(*)c2*)c2c(**)c2c1c(*)c(*)c(*)c2* 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- QLDLCDCMJQRQEU-UHFFFAOYSA-N 2',7'-dibromospiro[1-azapentacyclo[10.7.1.02,7.08,20.014,19]icosa-2,4,6,8(20),9,11,14,16,18-nonaene-13,9'-fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC3=C2N1C1=CC=CC=C1C31C2=CC(Br)=CC=C2C2=CC=C(Br)C=C21 QLDLCDCMJQRQEU-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 description 1
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 1
- UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical compound N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- PWSROGYYCPXIGK-UHFFFAOYSA-N spiro[benzo[c]fluorene-7,9'-fluorene] Chemical compound C1=CC=CC=2C3=CC=CC=C3C3(C=4C=CC=CC4C=4C5=C(C=CC34)C=CC=C5)C12 PWSROGYYCPXIGK-UHFFFAOYSA-N 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229950008188 sulfamidochrysoidine Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- 150000003536 tetrazoles Chemical class 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
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- 238000004506 ultrasonic cleaning Methods 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
L3は、直接結合;または置換もしくは非置換のアリーレン基であるか、R1と結合して置換もしくは非置換の環を形成し、
L4は、直接結合;または置換もしくは非置換のアリーレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R1は、水素;重水素;置換もしくは非置換のアルキル基;−OR;−SiRaRbRc;−OSiRaRbRc;置換もしくは非置換のアリール基;または−NRmRnであるか、L3と結合して置換もしくは非置換の環を形成し、
R2〜R8は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換のアルキル基;−OR;−SiRaRbRc;−OSiRaRbRc;置換もしくは非置換のアリール基;または−NRmRnであり、
R、Ra、Rb、Rc、RmおよびRnは、互いに同一または異なり、それぞれ独立して、水素、重水素、アルキル基、またはアリール基であり、
前記化学式1で表される化合物は、少なくとも1つの重水素を含み、
[化学式2]
HArは、置換もしくは非置換の含窒素ヘテロ環基であり、
Lは、直接結合;−O−;置換もしくは非置換の2価〜4価のアリール基;または置換もしくは非置換の2価〜4価のヘテロアリール基であり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
a1は、0〜3の整数であり、a1が2以上の場合、L1は、互いに同一または異なり、b1は、0〜3の整数であり、b1が2以上の場合、L2は、互いに同一または異なり、
aは、1または2であり、bは、1または2であり、bが2の場合、HArは、互いに同一または異なり、
a2は、1または2であり、b2は、1または2であり、
a2が2の場合、−[(L1)a1−(CN)a]は、互いに同一または異なり、
b2が2の場合、−[(L2)b1−(HAr)b]は、互いに同一または異なる。
(2)陽極/正孔注入層/正孔輸送層/発光層/陰極
(3)陽極/正孔輸送層/発光層/電子輸送層/陰極
(4)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(5)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(6)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(7)陽極/正孔輸送層/正孔調節層/発光層/電子輸送層/陰極
(8)陽極/正孔輸送層/正孔調節層/発光層/電子輸送層/電子注入層/陰極
(9)陽極/正孔注入層/正孔輸送層/正孔調節層/発光層/電子輸送層/陰極
(10)陽極/正孔注入層/正孔輸送層/正孔調節層/発光層/電子輸送層/電子注入層/陰極
(11)陽極/正孔輸送層/発光層/電子調節層/電子輸送層/陰極
(12)陽極/正孔輸送層/発光層/電子調節層/電子輸送層/電子注入層/陰極
(13)陽極/正孔注入層/正孔輸送層/発光層/電子調節層/電子輸送層/陰極
(14)陽極/正孔注入層/正孔輸送層/発光層/電子調節層/電子輸送層/電子注入層/陰極
2:陽極
3:有機物層
4:陰極
5:正孔注入層
6:正孔輸送層
6a:第1正孔輸送層
6b:第2正孔輸送層
7:正孔調節層
8:発光層
9:電子調節層
10:電子輸送層
11:電子注入層
12:電子注入および輸送層
Claims (11)
- 陽極と、
陰極と、
前記陽極と前記陰極との間に備えられた発光層と、
前記陰極と前記発光層との間に備えられた有機物層と
を含む
有機発光素子であって、
前記発光層は、下記化学式1で表される化合物を含み、
前記陰極と前記発光層との間に備えられた有機物層は、下記化学式2で表される化合物を含む
有機発光素子:
[化学式1]
L3は、直接結合;または置換もしくは非置換のアリーレン基であるか、R1と結合して置換もしくは非置換の環を形成し、
L4は、直接結合;または置換もしくは非置換のアリーレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R1は、水素;重水素;置換もしくは非置換のアルキル基;−OR;−SiRaRbRc;−OSiRaRbRc;置換もしくは非置換のアリール基;または−NRmRnであるか、L3と結合して置換もしくは非置換の環を形成し、
R2〜R8は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換のアルキル基;−OR;−SiRaRbRc;−OSiRaRbRc;置換もしくは非置換のアリール基;または−NRmRnであり、
R、Ra、Rb、Rc、RmおよびRnは、互いに同一または異なり、それぞれ独立して、水素;重水素;アルキル基;またはアリール基であり、
前記化学式1で表される化合物は、少なくとも1つの重水素を含み、
[化学式2]
Lは、直接結合;−O−;置換もしくは非置換の2価〜4価のアリール基;または置換もしくは非置換の2価〜4価のヘテロアリール基であり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
a1は、0〜3の整数であり、a1が2以上の場合、L1は、互いに同一または異なり、
b1は、0〜3の整数であり、b1が2以上の場合、L2は、互いに同一または異なり、
aは、1または2であり、
bは、1または2であり、
bが2の場合、HArは、互いに同一または異なり、
a2は、1または2であり、
b2は、1または2であり、
a2が2の場合、−[(L1)a1−(CN)a]は、互いに同一または異なり、
b2が2の場合、−[(L2)b1−(HAr)b]は、互いに同一または異なる。 - 前記R1〜R8の少なくとも1つが重水素である、
請求項1に記載の有機発光素子。 - 前記L3およびL4の少なくとも1つは、重水素化されたものである、
請求項1または2に記載の有機発光素子。 - 前記Ar1およびAr2の少なくとも1つが重水素;または重水素化されたアリール基である、
請求項1から3のいずれか1項に記載の有機発光素子。 - 前記Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、水素;重水素;重水素で置換もしくは非置換のフェニル基;重水素で置換もしくは非置換のナフチルフェニル基;重水素で置換もしくは非置換のビフェニル基;重水素で置換もしくは非置換のナフチル基;重水素で置換もしくは非置換のフェナントレニル基;重水素で置換もしくは非置換のフルオランテニル基;重水素で置換もしくは非置換のフェニルピリジニル基;重水素で置換もしくは非置換のジベンゾフラニル基;重水素で置換もしくは非置換のジベンゾチオフェニル基;または重水素で置換もしくは非置換のベンゾナフトチオフェニル基である、
請求項1から3のいずれか1項に記載の有機発光素子。 - 前記HArは、置換もしくは非置換のピリミジニル基;置換もしくは非置換のピリジニル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のカルバゾリル基;置換もしくは非置換のイミダゾリル基;置換もしくは非置換のベンズイミダゾリル基;置換もしくは非置換のフェナントロリニル基;置換もしくは非置換のベンゾ[4,5]イミダゾ[1,2−c]キナゾリニル基;置換もしくは非置換のベンゾ[4,5]イミダゾ[1,2−f]フェナントリジニル基;または置換もしくは非置換のスピロ[フルオレン−9,8'−インドロ[3,2,1−ジ]アクリジニル]基である、
請求項1から5のいずれか1項に記載の有機発光素子。 - 前記aは、2である、
請求項1から6のいずれか1項に記載の有機発光素子。 - 前記bは、2である、
請求項1から7のいずれか1項に記載の有機発光素子。 - 前記Lが置換もしくは非置換の2価〜4価のヘテロアリール基であるか、
前記L1およびL2の少なくともいずれか1つが置換もしくは非置換のヘテロアリーレン基である、
請求項1から8のいずれか1項に記載の有機発光素子。 - 前記化学式2で表される化合物を含む有機物層は、
電子注入層;
電子輸送層;
電子注入および輸送層;または
電子調節層である、
請求項1から10のいずれか1項に記載の有機発光素子。
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WO2020060320A1 (ko) | 2020-03-26 |
CN112136224A (zh) | 2020-12-25 |
KR20200033769A (ko) | 2020-03-30 |
US20210210694A1 (en) | 2021-07-08 |
JP7081742B2 (ja) | 2022-06-07 |
KR102234188B1 (ko) | 2021-03-31 |
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