WO2018131866A1 - Dispositif électroluminescent organique - Google Patents
Dispositif électroluminescent organique Download PDFInfo
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- WO2018131866A1 WO2018131866A1 PCT/KR2018/000398 KR2018000398W WO2018131866A1 WO 2018131866 A1 WO2018131866 A1 WO 2018131866A1 KR 2018000398 W KR2018000398 W KR 2018000398W WO 2018131866 A1 WO2018131866 A1 WO 2018131866A1
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- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- membered
- independently
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- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 40
- -1 pyridopyrimidinyl Chemical group 0.000 claims description 28
- 239000002019 doping agent Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 125000002723 alicyclic group Chemical group 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000005104 aryl silyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Chemical group 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 230000002829 reductive effect Effects 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 164
- 230000032258 transport Effects 0.000 description 66
- 239000000463 material Substances 0.000 description 63
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 21
- 238000007740 vapor deposition Methods 0.000 description 19
- 230000005525 hole transport Effects 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- AMSJIGYDHCSSRE-UHFFFAOYSA-N 3,14-diazahexacyclo[11.11.0.02,10.04,9.015,24.016,21]tetracosa-1(24),2,4,6,8,10,12,14,16,18,20,22-dodecaene Chemical compound C1=CC=C2C=CC3=C4C5=NC6=CC=CC=C6C5=CC=C4N=C3C2=C1 AMSJIGYDHCSSRE-UHFFFAOYSA-N 0.000 description 9
- 0 *C(C=*[C@@](*I)I*1C(C=C(C(C2)C3=C4CCCC=C/C=C/*3)*4N)=C2C2C1C=CC2)=* Chemical compound *C(C=*[C@@](*I)I*1C(C=C(C(C2)C3=C4CCCC=C/C=C/*3)*4N)=C2C2C1C=CC2)=* 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 150000003252 quinoxalines Chemical class 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 5
- 150000001555 benzenes Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 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 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 3
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910001632 barium fluoride Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- DWDHOTUTUOTLFA-UHFFFAOYSA-M cesium;quinoline-2-carboxylate Chemical compound [Cs+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 DWDHOTUTUOTLFA-UHFFFAOYSA-M 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-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
- 229910052697 platinum Inorganic materials 0.000 description 2
- JYILWUOXRMWVGD-UHFFFAOYSA-M potassium;quinoline-2-carboxylate Chemical compound [K+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 JYILWUOXRMWVGD-UHFFFAOYSA-M 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- PLTCLMZAIZEHGD-UHFFFAOYSA-M sodium;quinoline-2-carboxylate Chemical compound [Na+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 PLTCLMZAIZEHGD-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- HHKQGVNLHVCGQX-SKYPFOQVSA-N C#C/C=C(/C=CC=C1)\C1=C/Cc1nc(-c2cc3ccccc3cc2)nc(-c2cc(C3C=CC(c4cnccc4)=CC3)cc(-c(cc3)ccc3-c3cccnc3)c2)n1 Chemical compound C#C/C=C(/C=CC=C1)\C1=C/Cc1nc(-c2cc3ccccc3cc2)nc(-c2cc(C3C=CC(c4cnccc4)=CC3)cc(-c(cc3)ccc3-c3cccnc3)c2)n1 HHKQGVNLHVCGQX-SKYPFOQVSA-N 0.000 description 1
- AYFDATGWZURKNT-JAZJGKHYSA-N C(C1c2ccccc2)c(cc(c(c2c3ccc(-c4ccccc4)c2)c2)[n]3C([C@H](C3)c4ccccc4)=Nc4c3cccc4)c2-c2c1cc(cccc1)c1c2 Chemical compound C(C1c2ccccc2)c(cc(c(c2c3ccc(-c4ccccc4)c2)c2)[n]3C([C@H](C3)c4ccccc4)=Nc4c3cccc4)c2-c2c1cc(cccc1)c1c2 AYFDATGWZURKNT-JAZJGKHYSA-N 0.000 description 1
- ZBTMRWUILCELBS-UHFFFAOYSA-N C(Cc(cc(c(c1ccccc11)c2)[n]1-c1ccccc1)c2-c1c2cc(cccc3)c3c1)C2c1nc2ccccc2c(-c(cc2)ccc2-c2ccccc2)n1 Chemical compound C(Cc(cc(c(c1ccccc11)c2)[n]1-c1ccccc1)c2-c1c2cc(cccc3)c3c1)C2c1nc2ccccc2c(-c(cc2)ccc2-c2ccccc2)n1 ZBTMRWUILCELBS-UHFFFAOYSA-N 0.000 description 1
- MIHQAQYDRATRSB-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2ccccc2)nc(-c(cc2)cc3c2-c2c4[s]c5ccccc5c4ccc2C32c3ccccc3-c3ccccc23)n1 Chemical compound C1C=CC=CC1c1nc(-c2ccccc2)nc(-c(cc2)cc3c2-c2c4[s]c5ccccc5c4ccc2C32c3ccccc3-c3ccccc23)n1 MIHQAQYDRATRSB-UHFFFAOYSA-N 0.000 description 1
- AFAHSUPAZLXLKY-UHFFFAOYSA-N C1c(cc(c(c2ccccc22)c3)[n]2-c2ccccc2)c3-c2cc3ccccc3cc2C1c1nc2ccccc2c(-c2ccccc2)n1 Chemical compound C1c(cc(c(c2ccccc22)c3)[n]2-c2ccccc2)c3-c2cc3ccccc3cc2C1c1nc2ccccc2c(-c2ccccc2)n1 AFAHSUPAZLXLKY-UHFFFAOYSA-N 0.000 description 1
- GQXKSOPMJVCAER-UHFFFAOYSA-O CC(C1)(C(C2C=CC=CC22C)=CC3=C1[NH2+]C(c1ccccc1)N3c1ccccc1)N2c1cccc(C2=NC(C3(C)C=CC=CC3)NC(c3ccccc3)=N2)c1 Chemical compound CC(C1)(C(C2C=CC=CC22C)=CC3=C1[NH2+]C(c1ccccc1)N3c1ccccc1)N2c1cccc(C2=NC(C3(C)C=CC=CC3)NC(c3ccccc3)=N2)c1 GQXKSOPMJVCAER-UHFFFAOYSA-O 0.000 description 1
- KLVBNPUVEDAVTA-UHFFFAOYSA-N CC(C1)C=CC(c2ccccc22)=C1C2(c1ccccc1)c1ccc(c(cccc2)c2[n]2C(N(C)c3c4[o]c5ccccc35)N=C4C3=CCC(C)C(c4ccccc4)=C3)c2c1 Chemical compound CC(C1)C=CC(c2ccccc22)=C1C2(c1ccccc1)c1ccc(c(cccc2)c2[n]2C(N(C)c3c4[o]c5ccccc35)N=C4C3=CCC(C)C(c4ccccc4)=C3)c2c1 KLVBNPUVEDAVTA-UHFFFAOYSA-N 0.000 description 1
- KVRDKDXOSBWZBM-YQXGSSKCSA-N CC([C@@H]1c(cc2)ccc2-c2nc(cccc3)c3nc2C2(C)C=CC=CC2)C(CC(C)(C(c2cc(cccc3)c3cc22)=C3)N2c2ccccc2)=C3c2c1cccc2 Chemical compound CC([C@@H]1c(cc2)ccc2-c2nc(cccc3)c3nc2C2(C)C=CC=CC2)C(CC(C)(C(c2cc(cccc3)c3cc22)=C3)N2c2ccccc2)=C3c2c1cccc2 KVRDKDXOSBWZBM-YQXGSSKCSA-N 0.000 description 1
- AZRZIWWCUOWSLS-UHFFFAOYSA-N CC1(c2ccccc2)N=C(c(cc2)ccc2-[n]2c3c4[s]c5ccccc5c4ccc3c3ccccc23)N=C(c2ccccc2)N1 Chemical compound CC1(c2ccccc2)N=C(c(cc2)ccc2-[n]2c3c4[s]c5ccccc5c4ccc3c3ccccc23)N=C(c2ccccc2)N1 AZRZIWWCUOWSLS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGENZXANIROFSN-UHFFFAOYSA-N Cc(c1c2cccc1)c(-[n]1c3cc4ccccc4cc3c(cc3c4c5cccc4)c1cc3[n]5-c1ccccc1)nc2-c1cccc2ccccc12 Chemical compound Cc(c1c2cccc1)c(-[n]1c3cc4ccccc4cc3c(cc3c4c5cccc4)c1cc3[n]5-c1ccccc1)nc2-c1cccc2ccccc12 UGENZXANIROFSN-UHFFFAOYSA-N 0.000 description 1
- PWEALQXTXOKXCI-UHFFFAOYSA-N Cc1c(C)[o]c(cc2C3c(cccc4)c4C=CC33)c1cc2N3C1=NC(c2ccccc2)NC(c2ccccc2)=N1 Chemical compound Cc1c(C)[o]c(cc2C3c(cccc4)c4C=CC33)c1cc2N3C1=NC(c2ccccc2)NC(c2ccccc2)=N1 PWEALQXTXOKXCI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101001003146 Mus musculus Interleukin-11 receptor subunit alpha-1 Proteins 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
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- 230000008901 benefit Effects 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- XCKZSCADLOQGSK-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc1c1c2)c1cc1c2c2cc(cccc3)c3cc2[n]1-c1nc(cccc2)c2c(-c2cc(cccc3)c3c3c2cccc3)n1 Chemical compound c(cc1)ccc1-[n](c1ccccc1c1c2)c1cc1c2c2cc(cccc3)c3cc2[n]1-c1nc(cccc2)c2c(-c2cc(cccc3)c3c3c2cccc3)n1 XCKZSCADLOQGSK-UHFFFAOYSA-N 0.000 description 1
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- 238000002484 cyclic voltammetry Methods 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000003838 furazanyl group Chemical group 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
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- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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Images
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
Definitions
- the present disclosure relates to an organic electroluminescent device comprising a light-emitting layer and an electron transport zone.
- An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
- the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- An organic EL device changes electric energy into light by applying electricity to an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
- the organic layer of the OLED may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., if necessary.
- the materials used in the organic layer can be classified into a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on functions.
- a hole injection material a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
- holes from an anode and electrons from a cathode are injected into a light-emitting layer by the application of electric voltage, and an exciton having high energy is produced by the recombination of the holes and electrons.
- the organic light-emitting compound moves into an excited state by the energy and emits light from energy when the organic light-emitting compound returns to the ground state from the excited state
- the most important factor determining luminous efficiency in an organic EL device is light-emitting materials.
- the light-emitting materials are required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, and uniformality and stability of the formed light-emitting material layer.
- the light-emitting material is classified into blue, green, and red light-emitting materials according to the light-emitting color, and further includes yellow or orange light-emitting materials. Furthermore, the light-emitting material is classified into a host material and a dopant material in a functional aspect.
- an urgent task is the development of an OLED having high efficiency and long lifespan. In particular, the development of highly excellent light-emitting material over conventional materials is urgently required, considering the EL properties necessary for medium- and large-sized OLED panels.
- an electron transport material actively transports electrons from a cathode to a light-emitting layer and inhibits transport of holes which are not recombined in the light-emitting layer to increase recombination opportunity of holes and electrons in the light-emitting layer.
- electron-affinitive materials are used as an electron transport material.
- Organic metal complexes having light-emitting function such as Alq 3 are excellent in transporting electrons, and thus have been conventionally used as an electron transport material.
- Alq 3 has problems in that it moves to other layers and shows reduction of lifespan. Therefore, new electron transport materials have been required, which do not have the above problems, are highly electron-affinitive, and quickly transport electrons in organic EL devices to provide organic EL devices having high luminous efficiency.
- an electron buffer layer is equipped to improve a problem of light-emitting luminance reduction which may occur due to the change of current properties in the device when the device is exposed to a high temperature during a process of producing panels.
- the properties of the compounds comprised in the electron buffer layer are important.
- the compound used in the electron buffer layer is desirable to perform a role of controlling an electron injection by the electron withdrawing characteristics and the electron affinity LUMO (lowest unoccupied molecular orbital) energy level, and thus may perform a role to improve the efficiency and the lifespan of the organic electroluminescent device.
- Korean Patent Application Laid-Open No. 2015-0077513 discloses an organic electroluminescent device comprising a benzoindolocarbazole and quinoxaline derivative as a host and an imidazole derivative as an electron transport material.
- Korean Patent Application Laid-Open No. 2015-0071685 discloses an organic electroluminescent device comprising a carbazole derivative as a first host, a quinoxaline derivative as a second host, and an imidazole derivative as an electron transport material.
- Korean Patent No. 1511072 discloses an organic electroluminescent device comprising a benzoindolocarbazole derivative as a host, and Alq 3 as an electron transport material.
- Tetrahedron Letters 52, 6942 (2011) discloses an organic electroluminescent material comprising a quinoxaline derivative.
- the objective of the present disclosure is to provide an organic electroluminescent device having low driving voltage, high efficiency and/or long lifespan by comprising a specific combination of a light-emitting layer and an electron transport zone.
- the light-emitting layer comprising a phosphorescent dopant is advantageous in that the hole and electron current characteristics of the material of the light-emitting layer are high for low driving voltage, high efficiency and long lifespan, and that the material has excellent thermal stability in order to improve the lifespan.
- a charge trap is minimized by using a light-emitting material having a narrow energy band gap, thereby contributing to a driving voltage and a luminous efficiency.
- the derivatives of benzoindolocarbazole and quinoxaline of the present disclosure can have not only excellent thermal stability due to their twisted structure, but also a narrow energy band gap by controlling the position of a substituent.
- an organic electroluminescent device can have low driving voltage, high efficiency and/or long lifespan properties by comprising a derivative compound of benzoindolocarbazole and quinoxaline in a light-emitting layer and a heterocyclic derivative compound containing azines of the present disclosure in an electron transport zone.
- an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and an electron transport zone between the light-emitting layer and the second electrode, wherein the light-emitting layer comprises a compound represented by the following formula 1:
- L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene,
- X 1 to X 6 each independently, represent N or CR 3 , with a proviso that at least one of X 1 to X 6 represent N,
- Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl,
- R 1 to R 3 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxy, with a proviso that in at least one group of the adjacent two R 1 groups and the adjacent two R 2 groups, the adjacent two R
- R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, and
- a and b each independently, represent an integer of 1 to 4, where if a and b, each independently, are an integer of 2 or more, each of R 1 and R 2 may be the same or different; and
- the electron transport zone comprises a compound represented by the following formula 11:
- N 1 and N 2 each independently, represent N or CR 18 , with a proviso that at least one of N 1 and N 2 represent N,
- Y 1 to Y 4 each independently, represent N or CR 19 ,
- R 18 and R 19 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C50)aryl, a substituted or unsubstituted (3- to 50-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyl
- the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P;
- the heterocycloalkyl contains at least one heteroatom selected from O, S, and N.
- the present disclosure provides an organic electroluminescent device having low driving voltage, high efficiency and/or long lifespan, and a display system or a lighting system can be produced by using the device.
- Figure 1 illustrates a molecular structure of a compound represented by formula 1 according to an embodiment of the present disclosure in 3D form.
- Figure 2 illustrates the current efficiency of the organic electroluminescent devices of Comparative Example 1 and Device Example 3 with respect to the luminance.
- the present disclosure relates to an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and an electron transport zone between the light-emitting layer and the second electrode, wherein the light-emitting layer comprises a compound represented by formula 1, and the electron transport zone comprises a compound represented by formula 11.
- the electron transport zone may comprise at least one of an electron transport layer and an electron buffer layer, and the compound represented by formula 11 may be comprised in at least one of the electron transport layer and the electron buffer layer.
- the electron buffer layer may be comprised between the light-emitting layer and the electron transport layer, or between the electron transport layer and the second electrode.
- the organic electroluminescent device of the present disclosure comprises a substrate, a first electrode formed on the substrate, an organic layer formed on the first electrode, and a second electrode formed on the organic layer and facing the first electrode.
- the organic layer may comprise a hole injection layer, a hole transport layer formed on the hole injection layer, and a light-emitting layer formed on the hole transport layer.
- the organic layer may comprise an electron transport zone formed on the light-emitting layer, and the electron transport zone may comprise at least one of an electron transport layer, an electron injection layer and an electron buffer layer.
- Each of the electron transport layer, the electron injection layer, and the electron buffer layer may be composed of two or more layers.
- the organic layer may comprise an electron buffer layer formed on the light-emitting layer and an electron transport layer formed on the electron buffer layer, or may comprise an electron buffer layer or an electron transport layer formed on the light-emitting layer.
- L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene; more preferably, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene; and for example, a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, or an unsubstituted pyridinylene.
- X 1 to X 6 each independently, represent N or CR 3 , with a proviso that at least one of X 1 to X 6 represent N. According to one embodiment of the present disclosure, at least one of X 1 to X 6 may represent N, and X 2 to X 5 may represent CR 3 .
- the structure of may represent a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted pyridopyrimidinyl, or a substituted or unsubstituted pyridopyrazinyl; preferably, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted quinazolinyl, and wherein, * represents a bonding site with L 1 .
- Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; more preferably, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl; and for example, an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, a fluorenyl substituted with a dimethyl, an unsubstituted phenanthrenyl, or an unsubstituted pyridinyl.
- R 1 to R 3 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano, a nitro, or a hydroxy; preferably, hydrogen, or a substituted or unsubstituted (C6-C25)aryl; and
- R 1 and R 2 each independently, may represent hydrogen, or an unsubstituted phenyl
- R 3 may represent hydrogen, a phenyl unsubstituted or substituted with at least one methyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted naphthylphenyl, a fluorenyl substituted with a dimethyl, or an unsubstituted phenanthrenyl.
- the adjacent two R 1 or the adjacent two R 2 are linked to form at least one substituted or unsubstituted benzene ring.
- the adjacent two R 1 groups and the adjacent two R 2 groups are linked to the adjacent two R 1 or the adjacent two R 2 to form a substituted or unsubstituted benzene ring, and preferably, an unsubstituted benzene ring.
- R 3 may represent a substituted or unsubstituted (C6-C18)aryl.
- R 3 may represent hydrogen.
- R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
- a and b each independently, represent an integer of 1 to 4, and preferably an integer of 1 to 3. If a and b, each independently, are an integer of 2 or more, each of R 1 and R 2 may be the same or different.
- Formula 1 may be represented by any one of the following formulas 2 to 7.
- L 1 , Ar 1 , R 1 , R 2 , X 1 to X 6 , a and b are as defined in formula 1; and R 5 and R 6 are each independently identical to the definition of R 1 .
- c and d each independently, represent an integer of 1 to 6; preferably 1 or 2; and more preferably, 1. If c and d are an integer of 2 or more, each of R 5 and R 6 may be the same or different.
- N 1 and N 2 each independently, represent N or CR 18 , with a proviso that at least one of N 1 and N 2 represent N. According to one embodiment of the present disclosure, both N 1 and N 2 represent N.
- Y 1 to Y 4 each independently, represent N or CR 19 .
- Y 1 may represent N or CR 19
- Y 2 to Y 4 each independently, represent CR 19 .
- R 18 and R 19 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C50)aryl, a substituted or unsubstituted (3- to 50-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)
- R 18 and R 19 each independently, may represent hydrogen, a substituted or unsubstituted (C6-C40)aryl, or a substituted or unsubstituted (5- to 45-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C25) alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
- R 18 and R 19 each independently, may represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 40-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C18) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
- R 18 and R 19 each independently, may represent hydrogen, a substituted or unsubstituted phenyl, a substituted indole, a substituted or unsubstituted naphthyl, a substituted biphenyl, a substituted phenylnaphthyl, a substituted biphenylnaphthyl, a fluorenyl substituted with a dimethyl, an unsubstituted terphenyl, a substituted carbazolyl, a substituted benzocarbazolyl, an unsubstituted dibenzofuran, or a substituted or unsubstituted (16- to 38-membered)heteroaryl containing at least one of nitrogen, oxygen, and sulfur; or may be linked to an adjacent substituent to form an unsubstituted benzofuran ring.
- Formula 11 may be represented by the following formula 12:
- Y 1 is as defined in formula 11; A 1 and A 2 are each independently identical to the definition of R 19 of formula 11; and m represents 1 or 2.
- L 2 represents a single bond, a substituted or unsubstituted (C6-C50)arylene, or a substituted or unsubstituted (5- to 50-membered)heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C45)arylene, or a substituted or unsubstituted (5- to 45-membered)heteroarylene; more preferably, a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; and for example, a single bond, a phenylene unsubstituted or substituted with a pyridinyl(s), an unsubstituted naphthylene, an unsubstituted biphenylene, an unsubstituted phenylnaphthylene, an unsubsti
- Ar represents a substituted or unsubstituted (C6-C50)aryl, or a substituted or unsubstituted (5- to 50-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C45)aryl, or a substituted or unsubstituted (5- to 45-membered)heteroaryl; and more preferably, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 40-membered)heteroaryl.
- Ar may represent a phenyl unsubstituted or substituted with a pyridinyl(s), an unsubstituted naphthyl, a fluorenyl substituted with a dimethyl(s), an unsubstituted phenanthrenyl, an unsubstituted triphenylenyl, an unsubstituted pyridinyl, a benzimidazolyl substituted with a phenyl(s), an indolyl substituted with at least one phenyl, an unsubstituted quinolyl, a substituted or unsubstituted carbazolyl, an unsubstituted dibenzothiophenyl, an unsubstituted dibenzofuranyl, a benzocarbazolyl unsubstituted or substituted with a phenyl(s), an unsubstituted dibenzocarbazolyl, an unsubstituted benzo
- the substituent of the substituted carbazolyl may be at least one of a methyl, a phenyl, a dibenzothiophenyl, a dibenzofuranyl, a fluorenyl substituted with a phenyl, and a carbazolyl substituted with a phenyl.
- the substituent of the substituted (13- to 38-membered)heteroaryl may be at least one of a methyl, a tert -butyl, a phenyl, a naphthyl, and a biphenyl.
- the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P; and preferably, at least one heteroatom selected from N, O, and S.
- the heterocycloalkyl contains at least one heteroatom selected from O, S, and N.
- (C1-C30)alkyl is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6.
- the above alkyl may include methyl, ethyl, n -propyl, iso -propyl, n -butyl, iso -butyl, tert -butyl, etc.
- (C3-C30)cycloalkyl is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
- the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (3- to 7-membered)heterocycloalkyl is meant to be a cycloalkyl having 3 to 7 ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N.
- the above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
- (C6-C30)aryl(ene) is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15.
- the above aryl may be partially saturated, and may comprise a spiro structure.
- the above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
- the number of the ring backbone atoms is preferably 3 to 20, more preferably 5 to 15.
- the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure.
- the above heteroaryl(ene) may include a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisox
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent.
- the substituents may be at least one selected from the group consisting of a (C1-C20)alkyl; a (C6-C25)aryl unsubstituted or substituted with a (C1-C20)alkyl and/or a (3- to 30-membered)heteroaryl; and a (5- to 40-membered)heteroaryl unsubstituted or substituted with a (C1-C20)alkyl and/or a (C6-C25)aryl.
- the substituents may be at least one of a methyl, a tert -butyl, a phenyl unsubstituted or substituted with a pyridinyl, a naphthyl, a biphenyl, a dimethylfluorenyl, a phenylfluorenyl, a diphenylfluorenyl, a phenanthrenyl, a triphenylenyl, a pyridinyl, an indolyl substituted with a diphenyl, a benzimidazolyl substituted with a phenyl, a quinolyl, a substituted or unsubstituted carbazolyl, a dibenzofuranyl, a dibenzothiophenyl, a benzocarbazolyl unsubstituted or substituted with a phenyl, a dibenzocarbazolyl, a benzophenanthrothioph
- the compound represented by formula 1 includes the following compounds, but is not limited thereto.
- the compound represented by formula 11 includes the following compounds, but is not limited thereto.
- the compound of formula 1 according to the present disclosure may be produced by a synthetic method known to one skilled in the art, and for example, may be synthesized with reference to the following reaction schemes 1 to 6, but is not limited thereto.
- L 1 , Ar 1 , R 1 , R 2 , R 5 , R 6 , X 1 to X 6 , a, b, c, and d are as defined in formulas 1 to 7, and X is a halogen.
- the compound of formula 11 according to the present disclosure may be produced by a synthetic method known to one skilled in the art, but is not limited thereto.
- the light-emitting layer of the present disclosure may be formed by using a host compound and a dopant compound.
- the host compound may consist of the compound represented by formula 1 as a sole compound, or may further comprise conventional materials generally comprised in organic electroluminescent materials.
- the dopant compound is not particulary limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
- the dopant comprised in the organic electroluminescent device of the present disclosure may comprise the compounds represented by the following formulas 101 to 104, but is not limited thereto.
- L d is selected from the following structures:
- R 100 , R 134 , and R 135 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
- R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy, where R 106 to R 109 may be linked to adjacent R 106 to R 109 to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and R 120 to R
- R 124 to R 133 and R 136 to R 139 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl, where R 124 to R 127 may be linked to adjacent R 124 to R 127 to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
- X represents CR 21 R 22 , O, or S
- R 21 and R 22 each independently, represent a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
- R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a (C6-C30)aryl unsubstituted or substituted with an alkyl or deuterium, where R 208 to R 211 may be linked to adjacent R 208 to R 211 to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
- f and g each independently, represent an integer of 1 to 3; where if f or g is an integer of 2 or more, each R 100 may be the same or different; and
- n an integer of 1 to 3.
- the dopant compound includes the following compounds, but is not limited thereto.
- the dopant can be doped in an amount of less than 25 wt%, and preferably less than 17 wt%, based on the total amount of the dopant and host of the light-emitting layer.
- the light-emitting layer is composed of two or more layers, each of the layers may be prepared to emit color different from one another.
- the device may emit white light by preparing three light-emitting layers which emit blue, red, and green colors, respectively.
- the device may include light-emitting layers which emit yellow or orange color, if necessary.
- the electron buffer layer may include an electron buffer material comprising a compound represented by formula 11, or may comprise another electron buffer compound.
- the thickness of the electron buffer layer may be 1 nm or more, but is not particularly limited. Specifically, the thickness of the electron buffer layer may be in the range of from 2 nm to 200 nm.
- the electron buffer layer may be formed on the light-emitting layer by using known various methods such as vacuum deposition, wet film-forming methods, laser induced thermal imaging, etc.
- the electron buffer layer indicates a layer controlling an electron flow. Therefore, the electron buffer layer may be, for example, a layer which traps electrons, blocks electrons, or lowers an energy barrier between an electron transport zone and a light-emitting layer.
- the electron buffer layer may be comprised in an organic electroluminescent device which emits all colors such as blue, red, green, etc.
- the electron transport zone may comprise a compound represented by formula 11, an electron transport compound, a reductive dopant, or a combination thereof.
- the electron transport compound may be at least one selected from the group consisting of phenanthrene-based compounds, oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, anthracene-based compounds, aluminum complexes, and gallium complexes.
- the reductive dopant may be at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and halides, oxides, and complexes thereof.
- the reductive dopant includes lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li 2 O, BaO, and BaF 2 , but are not limited thereto.
- the electron transport layer may contain an electron transport material comprising a compound represented by formula 11.
- the electron transport layer may further comprise the reductive dopant described above.
- the electron injection layer may be prepared with an electron injection material known in the art, which includes lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li 2 O, BaO, and BaF 2 , but is not limited thereto.
- the organic electroluminescent device of the present disclosure is intended to explain one embodiment of the present disclosure, and is not meant in any way to restrict the scope of the invention.
- the organic electroluminescent device may be embodied in another way.
- any one optional component such as a hole injection layer, except for a light-emitting layer, may not be comprised in the organic electroluminescent device of the present disclosure.
- an optional component may be further comprised therein, which includes an impurity layer such as an n-doping layer and a p-doping layer.
- the organic electroluminescent device may be a both side emission type in which a light-emitting layer is placed on each of both sides of the impurity layer.
- the two light-emitting layers on the impurity layer may emit different colors.
- the organic electroluminescent device may be a bottom emission type in which a first electrode is a transparent electrode and a second electrode is a reflective electrode, or may be a top emission type in which a first electrode is a reflective electrode and a second electrode is a transparent electrode.
- the organic electroluminescent device may have an inverted type structure in which a cathode, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode are sequentially stacked on a substrate.
- LUMO energy level (A) and HOMO energy level are expressed in absolute values in the present disclosure.
- the values of the LUMO energy level are compared based on absolute values. Values measured by density functional theory (DFT) are used for LUMO energy levels and HOMO energy levels in the present disclosure.
- DFT density functional theory
- the LUMO energy levels may be easily measured by various known methods. Generally, LUMO energy levels are measured by cyclic voltammetry or ultraviolet photoelectron spectroscopy (UPS). Therefore, one skilled in the art may easily comprehend the electron buffer layer, light-emitting layer, and electron transport layer that satisfy the equational relationship of the LUMO energy levels of the present disclosure, and practice the present disclosure. HOMO energy levels may be easily measured in the same manner as LUMO energy levels.
- the LUMO energy level of the light-emitting layer (Ah) and the LUMO energy level of the electron transport zone (Ae) satisfy the following equation (1), wherein Ae refers to a LUMO energy level of the electron transport zone comprising an electron transport layer and/or an electron buffer layer.
- the donor and acceptor have a molecular structure that is mutually perpendicularly and horizontally twisted. That is, it can be confirmed that benzoindolocarbazole and quinoxaline have a dihedral angle close to 90°.
- This allows the device to exhibit bipolar properties through donor carbazole and electron deficient quinoxaline in the device, and to have excellent thermal stability and/or electrochemical properties due to its twisted structure.
- this structure enables effective charge transfer between the donor and the acceptor, and the following effects can be obtained. As shown in FIG.
- TICT Twisted Intramolecular Charge Transfer
- RISC reverse intersystem crossing
- T1 Twisted Intramolecular Charge Transfer
- a singlet CT state and a triplet CT state can be made into a state where small energy split occurs and they are mixed. This allows free energy transfer between singlet and triplet. That is, the transition from S1 to T1, or the transition from T1 to S1 can be made relatively free of each other. Using this mixed state of S1 and T1, the charges in the S1 and T1 states, which are eventually increased to TICT, can be easily transferred to the donor T1.
- a compound having a structure in which benzoindolocarbazole and quinoxaline are fused in the light-emitting layer has a chemical structure capable of increasing the generation efficiency from S1 to T1.
- the quinoxaline derivative exhibits a narrow energy bandgap characteristic due to strong electron-withdrawing characteristics. If the chemical structure of TICT is used, the quinoxaline derivative can have the characteristic of red migration, and the effect can be seen that the LUMO energy value is slightly lower. This can minimize the charge trap and build a more suitable energy level for the red host.
- a host having a TICT structure as described below has an excellent structure for improving thermal stability while reducing aggregation in a host because the molecular orientation is irregular, but the injection ability with respect to a planar orientation material may be relatively low in charge injection with other interface layers.
- the reason for this is that in the case of a planar orientation material, the charge transfer may be advantageous because the ⁇ - ⁇ overlap between neighboring molecules is increased and the positional disturbance is reduced, but in the case of a random orientation material, not only the state density (DOS) is widened but also the energy barrier becomes worse and the van der Waals intermolecular interaction becomes weak, which impedes the charge transfer, and current injection may not be easy. Also, the orientation effect can affect the degree of wave function overlap at the interface.
- DOS state density
- an azine-based heterocyclic derivative having a high electron affinity in the electron transport zone is used as an electron transport zone material, electron injection becomes easier, thereby increasing the driving voltage, efficiency and/or lifespan of the device.
- the electron current characteristic can be increased by utilizing the interface dipole formation and the charge transfer effect by using the material having excellent ability to accommodate the electron transfer zone in the light-emitting layer having the TICT structure. For example, by using electron transport layers of fused indolocarbazole-based (Donor) and azine-based (Accepter), charge injection through the CT effect at the interface can be facilitated.
- Magnetic dipole moments can result in greater charge transfer through the interface dipole in the case of organic molecules of a polar material.
- a compound used as the electron transport zone and a phenanthroxazole compound or a dibenzocarbazole compound as a HOMO orbital it has not only a large electronegativity and an electron-rich group, but also a rigid property as a structure in which groups such as phenanthrene and oxazole, or dibenzocarbazole are fused, and thus intermolecular transition is facilitated.
- the enhancement of intermolecular stacking facilitates the implementation of horizontal molecular orientation, thereby enabling rapid electronic current characteristics to be realized. This is effective in combination with the light-emitting layer, and can provide an organic electroluminescent device capable of realizing a high-purity color while having a relatively low driving voltage, and excellent luminous efficiency such as current efficiency and power efficiency.
- results according to the relationship of the LUMO energy levels of the electron transport zone (Ae) and the LUMO energy levels of the light-emitting layer (Ah) are for explaining the rough tendency of the device in accordance with the overall LUMO energy groups, and so results other than the above may be provided according to the inherent property of the specific derivatives, and the stability of the materials.
- OLED organic light-emitting diode
- An OLED device not according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropyl alcohol, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -7 torr.
- ITO indium tin oxide
- compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
- Compound HT-1 was then introduced into a cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
- Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
- a light-emitting layer was formed thereon as follows: Compound H-139 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-71 was introduced into another cell as a dopant.
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- compound ETL-1 (Alq 3 ) as an electron transport material was introduced into one cell of the vacuum vapor deposition apparatus and evaporated to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
- an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr.
- An OLED device was produced in the same manner as in Comparative Example 1, except that compound ETL-2 (BCP) instead of compound ETL-1 was used as an electron transport material.
- An OLED device was produced in the same manner as in Comparative Example 1, except that compound ETL-3 :compound EIL-1 in a weight ratio of 50:50 were evaporated to form an electron transport layer of 35 nm.
- OLED devices were produced in the same manner as in Comparative Example 3, except that the electron transport materials recited in Table 1 in a weight ratio of 50:50 were evaporated to form an electron transport layer.
- the driving voltage, luminous efficiency, and CIE color coordinates based on a luminance of 1,000 nits, and the time taken to be reduced from 100% to 90% of the luminance based on a luminance of 5,000 nits (lifespan; T90) of the OLED devices of Comparative Examples 1 to 3 and Device Examples 1 to 7 are provided in Table 1 below.
- a current efficiency versus a luminance of the OLED devices of Comparative Example 1 and Device Example 3 is illustrated in Figure 2 as a graph.
- OLED devices were produced in the same manner as in Comparative Example 3, except that the electron buffer material recited in Table 2 below was evaporated to form an electron buffer layer of 5 nm on the light-emitting layer, and the electron transport materials recited in Table 2 below in a weight ratio of 50:50 were evaporated to form an electron transport layer of 30 nm on the electron buffer layer.
- the driving voltage, luminous efficiency, and CIE color coordinates based on a luminance of 1,000 nits, and the time taken to be reduced from 100% to 80% of the luminance based on a luminance of 5,000 nits (lifespan; T80) of the OLED devices of Device Examples 8 to 10 are provided in Table 2 below.
- the OLED devices of Device Examples 1 to 10 which use a compound according to the present disclosure in a light-emitting layer, and an electron buffer layer and/or an electron transport layer, provide lower driving voltages, higher efficiencies and/or longer lifespans than those of Comparative Examples 1 to 3.
- An OLED device was produced in the same manner as in Device Example 7, except that compound HT-3 instead of compound HT-2 was used in the second hole transport layer, and compound EH-1 instead of compound H-139 was used in the light-emitting layer.
- An OLED device was produced in the same manner as in Comparative Example 4, except that compound H-139 was used in a light-emitting layer.
- the driving voltage, luminous efficiency, and CIE color coordinates based on a luminance of 1,000 nits, and the time taken to be reduced from 100% to 90% of the luminance based on a luminance of 5,000 nits (lifespan; T90) of the OLED devices of Comparative Example 4 and Device Example 11 are provided in Table 3 below.
- the OLED device of Device Example 11 in which a compound of the present disclosure was used in a light-emitting layer and an electron transport layer, provides lower driving voltage and longer lifespan compared to Comparative Example 4.
- an OLED device comprising a specific combination of compounds of the present disclosure may be suitable to flexible displays, lightings, and vehicle displays which require long lifespan.
- HOD Hole Only Device
- EOD Electron Only Device
- a ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
- Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -7 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 10 nm on the ITO substrate.
- Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the hole injection layer.
- compound HT-4 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 10 nm on the first hole transport layer.
- a light-emitting layer was formed thereon as follows: Compound H-139 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-71 was introduced into another cell as a dopant.
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the second hole transport layer.
- Compound HT-1 was then introduced into one cell of the vacuum vapor deposition apparatus and evaporated to form an electron blocking layer having a thickness of 20 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited on the electron blocking layer by another vacuum vapor deposition apparatus.
- an OLED device was produced.
- a voltage was 4.7 V at a current density of 10 mA/cm 2 and a voltage was 7.0 V at a current density of 100 mA/cm 2 .
- HBL hole blocking layer
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the hole blocking layer.
- Compound B-103 and compound EIL-1 were introduced into one cell and another cell of the vacuum vapor deposition apparatus, respectively, and the two materials were evaporated at the same rate and doped to a 50:50 weight ratio to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
- All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr.
- a device was produced in the same manner as in the EOD Example, except that compound ETL-1 was used instead of compound B-103 in the electron transport layer.
- a device was produced in the same manner as in the EOD Example, except that only compound ETL-1 was used in the electron transport layer.
- the voltage at current density of 10 mA/cm 2 , and the voltage at current density of 100 mA/cm 2 of the devices of the EOD Example, and EOD Comparative Examples 1 and 2 are provided in Table 4 below.
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Abstract
La présente invention concerne un dispositif électroluminescent organique. Le dispositif électroluminescent organique de la présente invention peut présenter une faible tension de commande, une efficacité élevée et/ou une longue durée de vie du fait qu'il comprenne une combinaison spécifique d'une couche électroluminescente et d'une zone de transport d'électrons.
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US16/468,587 US20190355912A1 (en) | 2017-01-10 | 2018-01-09 | Organic electroluminescent device |
CN202410254544.4A CN118159112A (zh) | 2017-01-10 | 2018-01-09 | 有机电致发光装置 |
CN201880005601.8A CN110121542A (zh) | 2017-01-10 | 2018-01-09 | 有机电致发光装置 |
JP2019534681A JP2020505755A (ja) | 2017-01-10 | 2018-01-09 | 有機エレクトロルミネセントデバイス |
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KR10-2017-0003673 | 2017-01-10 | ||
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KR1020180001844A KR102582797B1 (ko) | 2017-01-10 | 2018-01-05 | 유기 전계 발광 소자 |
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WO2015093878A1 (fr) * | 2013-12-18 | 2015-06-25 | Rohm And Haas Electronic Materials Korea Ltd. | Composé électroluminescent organique, et matériau hôte à composants multiples et dispositif électroluminescent organique comprenant ledit composé |
WO2015160224A1 (fr) * | 2014-04-18 | 2015-10-22 | Rohm And Haas Electronic Materials Korea Ltd. | Matériau hôte à plusieurs constituants et dispositif électroluminescent organique comprenant ledit matériau |
WO2016148390A1 (fr) * | 2015-03-13 | 2016-09-22 | Rohm And Haas Electronic Materials Korea Ltd. | Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux |
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WO2015093878A1 (fr) * | 2013-12-18 | 2015-06-25 | Rohm And Haas Electronic Materials Korea Ltd. | Composé électroluminescent organique, et matériau hôte à composants multiples et dispositif électroluminescent organique comprenant ledit composé |
WO2015160224A1 (fr) * | 2014-04-18 | 2015-10-22 | Rohm And Haas Electronic Materials Korea Ltd. | Matériau hôte à plusieurs constituants et dispositif électroluminescent organique comprenant ledit matériau |
WO2016148390A1 (fr) * | 2015-03-13 | 2016-09-22 | Rohm And Haas Electronic Materials Korea Ltd. | Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux |
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