KR20230153949A

KR20230153949A - 유기 화합물, 발광 디바이스, 발광 장치, 및 전자 기기

유기 화합물, 발광 디바이스, 발광 장치, 및 전자 기기 Download PDF

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Publication number: KR20230153949A
Authority: KR; South Korea
Prior art keywords: layer; organic compound; light; structural formula; film
Prior art date: 2022-04-29
Legal status : Pending

Application number

KR1020230055627A

Other languages

English (en)

Korean (ko)

Inventor

마사토시 다카바타케

유이 요시야스

사치코 가와카미

다케요시 와타베

노부하루 오사와

유코 구보타

Original Assignee

가부시키가이샤 한도오따이 에네루기 켄큐쇼

Priority date

2022-04-29

Filing date

2023-04-27

Publication date

2023-11-07

2023-04-27 Application filed by 가부시키가이샤 한도오따이 에네루기 켄큐쇼 filed Critical 가부시키가이샤 한도오따이 에네루기 켄큐쇼

2023-11-07 Publication of KR20230153949A publication Critical patent/KR20230153949A/ko

Status Pending legal-status Critical Current

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150000002894 organic compounds Chemical class 0.000 title claims abstract description 416
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 99
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 62
-1 deuterium) Chemical class 0.000 claims abstract description 48
125000003118 aryl group Chemical group 0.000 claims abstract description 29
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
125000003277 amino group Chemical group 0.000 claims abstract description 9
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
239000000758 substrate Substances 0.000 claims description 75
238000004891 communication Methods 0.000 claims description 21
229930195733 hydrocarbon Natural products 0.000 claims description 13
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 66
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 17
229910052805 deuterium Inorganic materials 0.000 abstract description 17
150000002431 hydrogen Chemical class 0.000 abstract description 12
239000010410 layer Substances 0.000 description 1318
239000010408 film Substances 0.000 description 384
239000000463 material Substances 0.000 description 209
238000000034 method Methods 0.000 description 208
238000002347 injection Methods 0.000 description 79
239000007924 injection Substances 0.000 description 79
230000006870 function Effects 0.000 description 70
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238000012545 processing Methods 0.000 description 46
238000010438 heat treatment Methods 0.000 description 44
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239000007789 gas Substances 0.000 description 35
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230000015572 biosynthetic process Effects 0.000 description 32
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239000000126 substance Substances 0.000 description 31
239000012298 atmosphere Substances 0.000 description 30
150000001875 compounds Chemical class 0.000 description 29
MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 29
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239000000203 mixture Substances 0.000 description 27
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
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238000001771 vacuum deposition Methods 0.000 description 15
239000002131 composite material Substances 0.000 description 14
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238000011179 visual inspection Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 12
238000000862 absorption spectrum Methods 0.000 description 12
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125000002883 imidazolyl group Chemical group 0.000 description 12
229910052741 iridium Inorganic materials 0.000 description 12
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TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
239000010409 thin film Substances 0.000 description 12
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230000000903 blocking effect Effects 0.000 description 11
230000008859 change Effects 0.000 description 11
238000005229 chemical vapour deposition Methods 0.000 description 11
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238000005260 corrosion Methods 0.000 description 11
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238000010586 diagram Methods 0.000 description 11
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
150000002430 hydrocarbons Chemical group 0.000 description 11
238000001459 lithography Methods 0.000 description 11
230000003287 optical effect Effects 0.000 description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
239000011701 zinc Substances 0.000 description 11
239000011787 zinc oxide Substances 0.000 description 11
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
125000005595 acetylacetonate group Chemical group 0.000 description 10
150000001339 alkali metal compounds Chemical class 0.000 description 10
238000001194 electroluminescence spectrum Methods 0.000 description 10
238000004770 highest occupied molecular orbital Methods 0.000 description 10
238000003384 imaging method Methods 0.000 description 10
229910052738 indium Inorganic materials 0.000 description 10
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
238000005259 measurement Methods 0.000 description 10
239000007769 metal material Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
238000001556 precipitation Methods 0.000 description 10
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
238000012360 testing method Methods 0.000 description 9
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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239000011777 magnesium Substances 0.000 description 8
150000004767 nitrides Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011241 protective layer Substances 0.000 description 8
YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 8
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 7
238000000605 extraction Methods 0.000 description 7
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PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 7
238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
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238000005424 photoluminescence Methods 0.000 description 7
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238000000859 sublimation Methods 0.000 description 7
230000008022 sublimation Effects 0.000 description 7
230000002194 synthesizing effect Effects 0.000 description 7
229910052718 tin Inorganic materials 0.000 description 7
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 7
229910052721 tungsten Inorganic materials 0.000 description 7
239000010937 tungsten Substances 0.000 description 7
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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238000010521 absorption reaction Methods 0.000 description 6
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125000005605 benzo group Chemical group 0.000 description 6
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
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IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
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238000002834 transmittance Methods 0.000 description 6
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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 5
AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
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DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
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238000004380 ashing Methods 0.000 description 5
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YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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239000002253 acid Substances 0.000 description 4
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
239000012670 alkaline solution Substances 0.000 description 4
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QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 4
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XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
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GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
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