WO2018117369A1 - Élément électroluminescent organique - Google Patents
Élément électroluminescent organique Download PDFInfo
- Publication number
- WO2018117369A1 WO2018117369A1 PCT/KR2017/009096 KR2017009096W WO2018117369A1 WO 2018117369 A1 WO2018117369 A1 WO 2018117369A1 KR 2017009096 W KR2017009096 W KR 2017009096W WO 2018117369 A1 WO2018117369 A1 WO 2018117369A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- unsubstituted
- substituted
- light emitting
- group
- organic light
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 78
- -1 biphenylyl Chemical group 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 35
- 239000002019 doping agent Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 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 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 3
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000000295 emission spectrum Methods 0.000 abstract description 12
- 239000010410 layer Substances 0.000 description 84
- 238000002360 preparation method Methods 0.000 description 66
- 239000002253 acid Substances 0.000 description 35
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 27
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 230000032258 transport Effects 0.000 description 15
- 229940126062 Compound A Drugs 0.000 description 14
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 14
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000011368 organic material Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000005605 benzo group Chemical group 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 0 **/C1=C(\C=C\I/C=C2/N*)/I/C2=C/C2=I=C1C=CC=C2*P Chemical compound **/C1=C(\C=C\I/C=C2/N*)/I/C2=C/C2=I=C1C=CC=C2*P 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000007614 solvation Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- SYACRXBYRNYMLN-UHFFFAOYSA-N 9-bromo-10-naphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 SYACRXBYRNYMLN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000007773 negative electrode material Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 1
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 description 1
- MVMKTVRVLIRKTJ-UHFFFAOYSA-N 1-azapentacyclo[10.6.1.02,7.08,19.013,18]nonadeca-2(7),3,5,8,10,12(19),13,15,17-nonaen-4-ylboronic acid Chemical compound C1=C2C=3C=CC=CC=3N3C2=C(C=C1)C1=CC=C(C=C13)B(O)O MVMKTVRVLIRKTJ-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- AEIPFESDNDUXNK-UHFFFAOYSA-N 9-bromo-10-(4-naphthalen-1-ylphenyl)anthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C=C1 AEIPFESDNDUXNK-UHFFFAOYSA-N 0.000 description 1
- VCJIOUBBOCVHPE-UHFFFAOYSA-N 9-bromo-10-(4-phenylphenyl)anthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C(C=C1)=CC=C1C1=CC=CC=C1 VCJIOUBBOCVHPE-UHFFFAOYSA-N 0.000 description 1
- FKIFDWYMWOJKTQ-UHFFFAOYSA-N 9-bromo-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 FKIFDWYMWOJKTQ-UHFFFAOYSA-N 0.000 description 1
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XPEUPRFLYMJDEG-UHFFFAOYSA-N CC1C#CC=C1 Chemical compound CC1C#CC=C1 XPEUPRFLYMJDEG-UHFFFAOYSA-N 0.000 description 1
- UXXWCYCBIWTDQB-UHFFFAOYSA-N CC1C=CC2C1C2 Chemical compound CC1C=CC2C1C2 UXXWCYCBIWTDQB-UHFFFAOYSA-N 0.000 description 1
- HINMTKAINNTPSW-PKTZIBPZSA-N C[C@@]1([C@]2(C=CC3)C(C)=C4C=C2)C3=CC=Cc2c1[n]4c1ccccc21 Chemical compound C[C@@]1([C@]2(C=CC3)C(C)=C4C=C2)C3=CC=Cc2c1[n]4c1ccccc21 HINMTKAINNTPSW-PKTZIBPZSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251556 Chordata Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 101100451713 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) HTL1 gene Proteins 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- CDJJKTLOZJAGIZ-UHFFFAOYSA-N Tolylacetate Chemical compound CC(=O)OC1=CC=C(C)C=C1 CDJJKTLOZJAGIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- KMGVRAOYNYQMEQ-UHFFFAOYSA-N [3-(5-phenylthiophen-2-yl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C=2SC(=CC=2)C=2C=CC=CC=2)=C1 KMGVRAOYNYQMEQ-UHFFFAOYSA-N 0.000 description 1
- JOSCNYCOYXTLTN-GFCCVEGCSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)CO JOSCNYCOYXTLTN-GFCCVEGCSA-N 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZUYJBCHDFCZUCF-UHFFFAOYSA-N c(cc-12)c-1c1c2[o]c2cc(cccc3)c3c(-c(c3c4)cccc3c(-c3ccccc3)c3c4c(-c4c(c(cccc5)c5[o]5)c5cc5ccccc45)ccc3)c12 Chemical compound c(cc-12)c-1c1c2[o]c2cc(cccc3)c3c(-c(c3c4)cccc3c(-c3ccccc3)c3c4c(-c4c(c(cccc5)c5[o]5)c5cc5ccccc45)ccc3)c12 ZUYJBCHDFCZUCF-UHFFFAOYSA-N 0.000 description 1
- MZNHDOVVFAAHIL-UHFFFAOYSA-N c(cc1)ccc1-c(c1ccc2)c(cccc3-c4cccc5c4c(c(cccc4)c4cc4)c4[o]5)c3cc1c2-c1cccc2c1c(c(cccc1)c1cc1)c1[o]2 Chemical compound c(cc1)ccc1-c(c1ccc2)c(cccc3-c4cccc5c4c(c(cccc4)c4cc4)c4[o]5)c3cc1c2-c1cccc2c1c(c(cccc1)c1cc1)c1[o]2 MZNHDOVVFAAHIL-UHFFFAOYSA-N 0.000 description 1
- AZRFAHZVCYHOBJ-UHFFFAOYSA-N c(cc1)ccc1-c(cccc1)c1-c(c1ccc2)c(cccc3-c4cc(cccc5)c5c5c4[o]c4ccccc54)c3cc1c2-c1c2[o]c(cccc3)c3c2c(cccc2)c2c1 Chemical compound c(cc1)ccc1-c(cccc1)c1-c(c1ccc2)c(cccc3-c4cc(cccc5)c5c5c4[o]c4ccccc54)c3cc1c2-c1c2[o]c(cccc3)c3c2c(cccc2)c2c1 AZRFAHZVCYHOBJ-UHFFFAOYSA-N 0.000 description 1
- NSZWVRBJIXCGRX-UHFFFAOYSA-N c(cc12)ccc1-c1ccccc1C2(c1ccc2)c(cccc3)c3-[n]3c1c2c1ccccc31 Chemical compound c(cc12)ccc1-c1ccccc1C2(c1ccc2)c(cccc3)c3-[n]3c1c2c1ccccc31 NSZWVRBJIXCGRX-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OWJXTQRIHCTGBZ-UHFFFAOYSA-N naphthalen-1-ylboronic acid;phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1.C1=CC=C2C(B(O)O)=CC=CC2=C1 OWJXTQRIHCTGBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- 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
- H10K2101/90—Multiple hosts in the emissive layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
Definitions
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
- the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
- the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- the light emitting layer of the organic light emitting device is composed of a light emitting dopant material which actually emits light with one or more host materials.
- the emission spectrum exhibits a unique emission spectrum for each of the materials of the light emitting dopant, a spectrum shift occurs due to the kind or combination of host materials to be used, and thus a desired color is often not obtained. Accordingly, in the organic light emitting device using the color filter, the light filter does not meet the light transmission range of the color filter, resulting in a problem in that the efficiency is reduced. In addition, even in the organic light emitting device that does not use a color filter, a color different from the color of the actually intended light emitting dopant is generated, causing problems in color or luminance. Accordingly, the present inventors confirmed the present invention by identifying an organic light emitting device that can solve the above problems as described below.
- Patent Document 0001 Korean Patent Publication No. 10-2000-0051826 ' ⁇ Contents of the Invention ⁇
- the present invention is to provide an organic light emitting device without distortion of the emission spectrum.
- the present invention is an anode; cathode; And a light emitting layer between the anode and the cathode, wherein the light emitting layer includes a compound having a dipole moment value of 4.5 or less as a first host.
- the organic light emitting device can provide an organic light emitting device without distortion of the emission spectrum by using a material of a host and a dopant satisfying a specific dipole moment value.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4.
- FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4.
- An example of the organic light emitting element made is shown.
- the term "substituted or unsubstituted" is deuterium; halogen; nitrile; nitro, hydroxy, carbonyl; ester, imide; amino; phosphine oxide; alkoxy; aryloxy; Alkylthioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkyl An amine group; heteroarylamine group; arylamine group; arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, 0 and S atoms, Substituted or two unsubstituted or two unsubstituted.
- the compound may have a structure as follows.
- the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
- a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms may be a compound of the following structural formula,
- carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the silyl group includes trimethylsilyl group, triethylsilyl group, t_butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
- the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
- alkyl group examples include methyl, ethyl, propyl, n-propyl, micropropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl 1-methyl-butyl, 1-ethyl-butyl, pentyl, n- Pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2 ⁇ prop
- the alkenyl number may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Another one According to an exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2, 2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl—1-hexyl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In a according to an embodiment of 'the number of carbon atoms of the cycloalkyl group has from 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
- aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
- the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
- the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
- the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
- the heterocyclic group is a heterocyclic group including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
- heterocyclic groups include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group and triazole group.
- the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
- the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
- the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
- the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
- the description of the aryl group described above may be applied.
- the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
- the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that the two substituents are bonded to each other.
- the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
- the present invention the anode; cathode; And a light emitting insect between the anode and the cathode, wherein the light emitting layer includes, as a host, a compound having a dipole moment value of 4.5 or less as a host.
- the shift of the emission spectrum of the dopant may occur depending on the type or combination of hosts included in the light emitting layer of the organic light emitting element. This is due to the solid state solvation effect (sol id state solvat ion ef fect) generated by the dipole moment of the host, and fails to obtain the intended emission spectrum, causing problems such as defects and reduced efficiency.
- the present invention is characterized in that a compound having a dipole moment value of 4.5 or less is used as a host of the light emitting layer so that the shift of the emission spectrum of the light emitting layer of the organic light emitting device is minimized.
- dipole moment means a physical quantity indicating the degree of polarity, and may be calculated as in Equation 3 below.
- the molecular density (molecular densi ty) can be obtained by calculation, and the value of the dipole moment can be obtained.
- the molecular density can be obtained by calculating charges and dipoles for each atom using the Hirshfeld Charge Analysis method, and calculating them according to the following equation, and the dipole moment ( Dipole Moment).
- the light emitting layer comprises a light emitting dopant
- the host and the light emitting dopant satisfy the following Equation 1:
- DM host and DM (light emitting dopant) are the dipole moment values of the host and the light emitting dopant, respectively,
- fh means the weight of the host divided by the total weight of the host and the light emitting dopant
- the light emitting layer includes n different materials, wherein n is an integer of 2 or more, at least one of the n materials is a light emitting dopant, and the n materials satisfy the following Equation 2. do:
- Ai denotes the weight of each substance divided by the total weight of the n substances.
- n is 2, 3, or 4. That is, the light emitting layer of the organic light emitting device according to the present invention, the dipole moment value is
- the compounds having 4.5 or less may include compounds having a dipole moment value of more than 4.5, but the total dipole moment value should be 4.5 or less depending on their concentration.
- a compound having a dipole moment value of 4.5 or less may be used, and for example, a compound represented by the following Chemical Formula 1, or a compound represented by the following Chemical Formula 2 may be used:
- Ar n and 12 are, each independently, a substituted or unsubstituted C 6 - C 2 containing 60 aryl, or a substituted or unsubstituted one or more heteroatoms selected from the group consisting of unsubstituted N eu 0 and S - 60 Heteroaryl,
- Ln and L 12 are each independently a single bond or a substituted or unsubstituted
- 3 ⁇ 4 is each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; C HO haloalkyl; Substituted or unsubstituted
- h and i are each independently 1 or 2
- X is an integer from 0 to 8
- Ar 2 i, Ar 22 and Ar 23 each independently include one or more heteroatoms selected from the group consisting of substituted or unsubstituted C 6 60 aryl, or substituted or unsubstituted N, 0 and 3 60 is a heteroaryl, - C 2
- L 21 , L 22 and L 23 are each independently a single bond or a substituted or unsubstituted C 6 -60 arylene,
- 3 ⁇ 4 is each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted alkyl; Substituted or unsubstituted haloalkyl; Substituted or unsubstituted d— 60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; A substituted or unsubstituted C 2 -60 alkenyl group; Substituted or unsubstituted C 6 -60 aryloxy; Substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted amines; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C 2 -60 heterocyclic group containing at least one of 0, N, Si and S,
- n, n and 0 are each independently 1 or 2
- the light-emitting insect includes both the compound represented by Formula 1 and the compound represented by Formula 2 as a host.
- the compound represented by Chemical Formula 1 has an anthracene structure, and is characterized by having a small dipole moment value by replacing an aromatic ring or a heteroaromatic ring at positions 9 and 10 of anthracene.
- Ar u and 12 are each independently phenyl , naphthyl Biphenylyl, or a group consisting of: wherein Ar u and ⁇ 12 are unsubstituted:
- L u and L 12 are each independently a single bond, phenylene, naphthylene, anthracenylene, or thiophenylene.
- the compound represented by Formula 1 is any one compound selected from the group consisting of:
- the production method is a reaction for introducing a substituent into No. 9 or No. 10 of anthracene as a Suzuki coupling reaction, which may be more specific in the production examples described later.
- the compound represented by Chemical Formula 2 has an anthracene structure, an aromatic ring or a heteroaromatic ring is substituted at positions 1 and 8 of the anthracene, and an aromatic ring or heteroaromatic ring is substituted at the position 10, thereby reducing a small dipole moment value.
- Ar 21 , Ar 22 and Ar 23 are each independently selected from phenyl, dimethylphenyl, naphthyl, biphenylrin, terphenyl, or a group consisting of:
- 3 ⁇ 4 is S, 0, N (R 3 ), or C (R4) (R 5 )
- 3 ⁇ 4 are, each independently, a substituted or non-substituted d-60 alkyl, substituted or unsubstituted C 6 unsubstituted - 60 aryl, or R4 and together are a substituted or unsubstituted Forms C 6 -60 aryl.
- Ar 21 and ⁇ 22 are the same as each other.
- L 21 , L 22 and L 23 are each independently a single bond, phenylene, or naphthylenyl.
- the compound represented by Formula 2 is any one compound selected from the group consisting of:
- the compound represented by Chemical Formula 2 may be prepared by the same method as in Banung Formula 2.
- the manufacturing method may be more specific in the production examples to be described later.
- the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
- the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ⁇ : ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene KPED0T), polypyri and polyaniline, and the like, but are not limited thereto.
- As the negative electrode material an electron is easily injected into the organic material layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
- Hole injection layer includes metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
- the organic light emitting device may include a hole injection layer for injecting holes from the electrode.
- the hole injection material it has the ability to transport holes, has an effect of hole injection at the anode, excellent hole injection effect on the light emitting layer or light emitting material, and prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material.
- the compound excellent in the thin film formation ability is preferable. It is preferable that the HOMCKhighest occupied molecular orbital of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
- hole injecting materials include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- Hole transport layer includes metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the organic light emitting device may include a hole transport layer that receives holes from an anode or a hole injection layer and transports holes to the light emitting layer.
- a material for transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material a material having high mobility to holes is suitable.
- Specific examples include arylamine-based organic materials, conductive polymers, and Block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the light emitting layer of the organic light emitting device according to the present invention may include a dopant in addition to the host described above.
- Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
- aromatic amine derivative a condensed aromatic ring having a substituted or unsubstituted arylamino group
- the derivative examples include pyrene, anthracene, chrysene and periplanthene having an arylamino group
- the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine.
- Substituents which are selected from 1 or 2 ′ or more from the group consisting of silyl groups, alkyl groups, cycloalkyl groups and arylamino groups are substituted or unsubstituted.
- the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
- the compound represented by the following Formula 3 may be used as the dopant:
- Ri to 3 ⁇ 4 are each independently hydrogen, halogen, substituted or unsubstituted
- An to Ar 4 are each independently a substituted or unsubstituted C 6 - C 2 containing 30 aryl or a substituted or unsubstituted 0, N, Si and S 1 out of more than 60 heterocyclic contribution, provided that, A to At least one of Ar 4 is represented by the following general formula (4):
- X is 0 or S
- R 9 and R 10 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d- 60 haloalkyl; Substituted or unsubstituted alkoxy; Substituted or unsubstituted d- 60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted C 2 -60 alkenyl; Substituted or unsubstituted C 6 — eo aryloxy; Substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted amines; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C 2 -60 heterocyclic group containing at least one of
- the organic light emitting device may include an electron transport layer that receives electrons from a cathode or an electron injection layer and transports electrons to the light emitting layer.
- an electron transport layer that receives electrons from a cathode or an electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- cathode materials are conventional materials having a low work function followed by an aluminum or silver layer— specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum or silver layer in each case.
- Electron injection layer is conventional materials having a low work function followed by an aluminum or silver layer— specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum or silver layer in each case.
- the organic light emitting device may include an electron injection layer for injecting electrons from an electrode.
- the electron injection material has the ability to transport electrons, has the effect of electron injection from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, prevents the excitation of the excitons generated in the light emitting layer to the hole injection layer, and
- the compound which is excellent in thin film formation ability is preferable.
- polonorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, Perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10—hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( Ecrezolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl ⁇ 8-quinolinato) (2-naprlato) gallium Or not limited thereto.
- Organic light emitting device examples include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tri
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4.
- FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4.
- An example of an organic light emitting device is shown.
- the organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configuration. At this time, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporat ion.
- PVD physical vapor deposition
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the light emitting layer may be formed of a host and a dopant not only by vacuum deposition but also by solution coating.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
- an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (W0 2003/012890).
- the manufacturing method is not limited thereto.
- the organic light emitting device according to the invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
- preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited thereto.
- reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distillation under reduced pressure, and recrystallized with Tol (luluene) / EA (ethyl acetate) to prepare a compound (12.8 g). , 93%) was prepared.
- Example 1-18 A compound was prepared.
- step 2 of Preparation Example 2-1 naphthalene—1 yl ylbonmic acid was used instead of di benzo [b, d] fur an-4-ylboronic acid. ”In step 4, di benzo [instead of naphthalene-1- ylboronic acid. b, d] f ur an-4-y 1 bor on ic acid, to prepare a compound of Preparation Example 2-2.
- Step 4 of Preparation Example 2-1 compound of Preparation Example 2-3 was prepared by using d i benzo [b, d] f ur an-4-y 1 bor on i c acid instead of naphthalene—1-ylboronic acid.
- step 4 of Preparation Example 2-1 a compound of Preparation Example 2-10 was prepared using naphthalene—1-ylboronic acid phenylboronic acid.
- step 2 of Preparation Example 2-1 napht ha 1 ene- 1-y 1 bor on ic acid was used instead of dibenzo [b, d] fur n-4-ylboronic acid, and naphtha 1 ene- (1,1'-biphenyl) 2-ylboronic acid was used instead of 1-ylboronic acid to prepare Preparation Example 2-46.
- step 2 of Preparation Example 2-1 instead of dibenzo [b, d] f ur an-4-ylboroni c acid, (3, 5-dimethy 1 pheny 1) bor on ic acid was used, and in step 4 napht pheny lboronic acid was used instead of ha 1 ene-1 ylboronic acid to prepare Preparation Example 2—47.
- Step 2 of Preparation Example 2-1 naphthalene-l-ylboronic acid was used instead of dibenzo [b, d] fur an-4-y lboronic acid to prepare Preparation Example 2-50.
- MS [M + ] found 556.63, calc. 556.22
- Step 2 of Preparation Example 2-1 instead of dibenzo [b, d] furan-4-ylboronic acid (9, 9-di pheny 1 -9H-f 1 uor en-4-y 1) bor on ic acid
- step 4 pheny 1 bor on ic acid was used instead of naphthalene-l-ylboronic acid, to prepare Preparation Example 2-51.
- Step 2 of Preparation Example 2-1 instead of dibenzo [b, d] f uran-4-ylboroni c acid (9, 9-di pheny 1 -9H- f 1 uor en-4-y 1) bor on ic acid
- dibenzo [b, d] furan I 4 ⁇ ylboronic acid was used to prepare a compound of Preparation Example 2-52.
- a glass substrate coated with a thin film having an indium tin oxide (ITO) of 150 nm was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
- ITO indium tin oxide
- Fischer Co. product was used as the detergent
- distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water.
- ultrasonic washing was performed twice with distilled water for 10 minutes.
- ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, and drying Transported.
- the substrate was cleaned for 5 minutes using nitrogen plasma, and then the substrate was transferred to a vacuum evaporator.
- HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm on the prepared IT0 transparent electrode to form a hole injection layer.
- HTL1 was thermally vacuum deposited to a thickness of 100 nm
- HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer.
- BH1 as a host and BD (weight ratio 95: 5) as a dopant were simultaneously vacuum deposited to form a light emitting layer having a thickness of 20 nm.
- ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer.
- LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer.
- aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting device.
- the organic light emitting device was manufactured by the same method as Example 1, but using the material and the content of the following Table 1 and 2 as the host and the dopant. 1-13, 2-1, etc., corresponding to the materials of Tables 1 and 2 below, mean that the compounds prepared in each preparation example are used, and the total EML of DM is obtained by multiplying the content of the dipole moment of each host and dopant by the content. Calculated in total.
- Example 57 1-38 0,07 0.200 2-47 1,12 0.150 BH3 4,92 m 0.68 DM 3.i? Examples 5S 1-3 $ 0.33 2-48 1.40 0.050 BH4 5.15 0,300 0.68 0.05 1.85 Example 59 1-43 0.12 0.800 2-49 1.18 0,050 BH5 5.57 O.D.
- the total light emitting layer DM of Example 1 and Example 2 was 0.09 and 4.47, respectively, and the total light emitting layer DM of Comparative Example 1 was 4.93.
- the peak max positions of the spectra are 458 nm, 464 nm, and 476 nm in the order of Example 1, Example 2, and Comparative Example 1, respectively. Moving toward longer wavelengths, the FWHM increases rapidly when the dipole moment of the host exceeds 4.5.
- Examples 1, 2 and Comparative Example 1 are (0.137, 0.092), (0.131, 0.152) and (0.156, 0.22), respectively. )
- the dipole moment value of the host exceeds 4.5, the spectrum shifts to longer wavelengths and the color purity rapidly deteriorates due to the increase in FWHM.
- Substrate 2 Anode
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
La présente invention concerne un élément électroluminescent organique n'ayant pas de distorsion d'un spectre d'émission.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201780002448.9A CN108463535B (zh) | 2016-12-20 | 2017-08-21 | 有机发光元件 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020160174931A KR102145024B1 (ko) | 2016-12-20 | 2016-12-20 | 유기 발광 소자 |
KR10-2016-0174931 | 2016-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2018117369A1 true WO2018117369A1 (fr) | 2018-06-28 |
Family
ID=62626759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2017/009096 WO2018117369A1 (fr) | 2016-12-20 | 2017-08-21 | Élément électroluminescent organique |
Country Status (3)
Country | Link |
---|---|
KR (1) | KR102145024B1 (fr) |
CN (1) | CN108463535B (fr) |
WO (1) | WO2018117369A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020075759A1 (fr) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique l'utilisant |
WO2020209293A1 (fr) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique le comprenant |
WO2020209292A1 (fr) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Élément électroluminescent organique et appareil électronique équipé de celui-ci |
CN112996779A (zh) * | 2019-02-20 | 2021-06-18 | 株式会社Lg化学 | 蒽衍生物和使用其的有机电子器件 |
US20220013737A1 (en) * | 2018-11-05 | 2022-01-13 | Samsung Display Co., Ltd. | Organic light-emitting device |
WO2022163626A1 (fr) * | 2021-01-26 | 2022-08-04 | 出光興産株式会社 | Composition, poudre, élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique et dispositif électronique |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200373496A1 (en) * | 2017-09-19 | 2020-11-26 | Lg Chem, Ltd. | Organic light emitting element |
CN108997345B (zh) * | 2018-08-20 | 2024-08-02 | 上海弗屈尔光电科技有限公司 | 一种氮杂螺环化合物及含有该化合物的有机光电器件 |
KR102299734B1 (ko) | 2018-10-16 | 2021-09-09 | 주식회사 엘지화학 | 유기 화합물 및 이를 포함하는 유기 발광 소자 |
WO2020209299A1 (fr) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Élément électroluminescent organique, et dispositif électronique le comprenant |
CN113631543A (zh) | 2019-04-08 | 2021-11-09 | 出光兴产株式会社 | 有机电致发光元件和使用其的电子设备 |
WO2020209307A1 (fr) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Élément électroluminescent organique, dispositif électronique et composé |
KR102427162B1 (ko) * | 2019-11-11 | 2022-07-29 | 주식회사 엘지화학 | 유기 발광 소자 |
EP3998322B1 (fr) * | 2019-12-26 | 2024-04-17 | Idemitsu Kosan Co., Ltd. | Élément électroluminescent organique, composition, poudre, équipement électronique et nouveau composé |
CN113666929B (zh) * | 2021-09-08 | 2023-04-07 | 南京高光半导体材料有限公司 | 一种含有咔唑芴类螺环化合物及有机电致发光器件 |
CN115611873A (zh) * | 2022-12-20 | 2023-01-17 | 吉林省元合电子材料有限公司 | 一种含有苯并咪唑和蒽结合结构的有机光电功能材料及其应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20020059256A (ko) * | 2001-01-02 | 2002-07-12 | 로버트 디. 크루그 | 개선된 휘도 효율을 갖는 유기 발광 다이오드 장치 |
KR20060121288A (ko) * | 2004-01-08 | 2006-11-28 | 이스트맨 코닥 캄파니 | 아미노안트라센을 사용한 안정한 유기 발광 디바이스 |
KR20140121123A (ko) * | 2013-04-05 | 2014-10-15 | 에스에프씨 주식회사 | 헤테로아릴기를 포함하는 아민기가 치환된 비대칭 피렌 유도체 및 이를 포함하는 유기 발광 소자 |
KR20160049500A (ko) * | 2014-10-27 | 2016-05-09 | 주식회사 엘지화학 | 유기 전계 발광 소자 |
KR20160052526A (ko) * | 2013-09-06 | 2016-05-12 | 이데미쓰 고산 가부시키가이샤 | 안트라센 유도체 및 그것을 사용한 유기 전계 발광 소자 |
US9437833B2 (en) * | 2011-08-30 | 2016-09-06 | Konica Minolta, Inc. | Organic electroluminescence element |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100430549B1 (ko) | 1999-01-27 | 2004-05-10 | 주식회사 엘지화학 | 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법 |
JP4984891B2 (ja) * | 2004-07-02 | 2012-07-25 | Jnc株式会社 | 発光材料およびこれを用いた有機電界発光素子 |
KR101115255B1 (ko) * | 2008-07-11 | 2012-02-15 | 주식회사 엘지화학 | 신규한 안트라센 유도체 및 이를 이용한 유기전자소자 |
US8431250B2 (en) * | 2009-04-24 | 2013-04-30 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescent element comprising the same |
KR20120135501A (ko) * | 2012-10-29 | 2012-12-14 | 에스에프씨 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US9947879B2 (en) * | 2013-03-15 | 2018-04-17 | Idemitsu Kosan Co., Ltd. | Anthracene derivative and organic electroluminescence element using same |
KR102316683B1 (ko) * | 2015-01-21 | 2021-10-26 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102100008B1 (ko) * | 2016-04-12 | 2020-04-10 | 주식회사 엘지화학 | 안트라센계 화합물 및 이를 포함하는 유기 발광 소자 |
KR101869657B1 (ko) * | 2016-08-09 | 2018-06-21 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기전계 발광 소자 |
KR101899728B1 (ko) * | 2016-09-07 | 2018-09-17 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
-
2016
- 2016-12-20 KR KR1020160174931A patent/KR102145024B1/ko active IP Right Grant
-
2017
- 2017-08-21 WO PCT/KR2017/009096 patent/WO2018117369A1/fr active Application Filing
- 2017-08-21 CN CN201780002448.9A patent/CN108463535B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20020059256A (ko) * | 2001-01-02 | 2002-07-12 | 로버트 디. 크루그 | 개선된 휘도 효율을 갖는 유기 발광 다이오드 장치 |
KR20060121288A (ko) * | 2004-01-08 | 2006-11-28 | 이스트맨 코닥 캄파니 | 아미노안트라센을 사용한 안정한 유기 발광 디바이스 |
US9437833B2 (en) * | 2011-08-30 | 2016-09-06 | Konica Minolta, Inc. | Organic electroluminescence element |
KR20140121123A (ko) * | 2013-04-05 | 2014-10-15 | 에스에프씨 주식회사 | 헤테로아릴기를 포함하는 아민기가 치환된 비대칭 피렌 유도체 및 이를 포함하는 유기 발광 소자 |
KR20160052526A (ko) * | 2013-09-06 | 2016-05-12 | 이데미쓰 고산 가부시키가이샤 | 안트라센 유도체 및 그것을 사용한 유기 전계 발광 소자 |
KR20160049500A (ko) * | 2014-10-27 | 2016-05-09 | 주식회사 엘지화학 | 유기 전계 발광 소자 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020075759A1 (fr) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique l'utilisant |
US20220013737A1 (en) * | 2018-11-05 | 2022-01-13 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN112996779A (zh) * | 2019-02-20 | 2021-06-18 | 株式会社Lg化学 | 蒽衍生物和使用其的有机电子器件 |
CN112996779B (zh) * | 2019-02-20 | 2024-08-02 | 株式会社Lg化学 | 蒽衍生物和使用其的有机电子器件 |
WO2020209293A1 (fr) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique le comprenant |
WO2020209292A1 (fr) * | 2019-04-08 | 2020-10-15 | 出光興産株式会社 | Élément électroluminescent organique et appareil électronique équipé de celui-ci |
WO2022163626A1 (fr) * | 2021-01-26 | 2022-08-04 | 出光興産株式会社 | Composition, poudre, élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique et dispositif électronique |
Also Published As
Publication number | Publication date |
---|---|
CN108463535A (zh) | 2018-08-28 |
KR102145024B1 (ko) | 2020-08-14 |
KR20180071850A (ko) | 2018-06-28 |
CN108463535B (zh) | 2021-01-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6638160B2 (ja) | 新規なヘテロ環化合物およびこれを利用した有機発光素子 | |
WO2018117369A1 (fr) | Élément électroluminescent organique | |
JP6733882B2 (ja) | 含窒素化合物およびこれを含む有機発光素子 | |
KR102111149B1 (ko) | 유기 발광 소자 | |
JP6673544B2 (ja) | ヘテロ環化合物およびこれを含む有機発光素子 | |
KR102099002B1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
JP2018532688A (ja) | 新規なヘテロ環式化合物およびこれを利用した有機発光素子 | |
JP6679092B2 (ja) | スピロ型化合物およびこれを含む有機電子素子 | |
KR102052710B1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 | |
JP6614520B2 (ja) | 化合物およびこれを含む有機電子素子 | |
KR102064992B1 (ko) | 신규한 헤테로고리 화합물 및 이를 이용한 유기발광 소자 | |
JP6624284B2 (ja) | アミン化合物およびこれを含む有機発光素子 | |
JP6750784B2 (ja) | 化合物およびこれを含む有機電子素子 | |
JP2020510652A (ja) | 新規な化合物およびこれを用いた有機発光素子 | |
CN110536887B (zh) | 新型化合物及包含其的有机发光器件 | |
JP6958967B2 (ja) | ヘテロ環化合物およびこれを含む有機発光素子 | |
KR20170037522A (ko) | 아민계 화합물 및 이를 포함하는 유기 발광 소자 | |
KR102088507B1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 | |
JP2018531232A6 (ja) | アミン化合物およびこれを含む有機発光素子 | |
KR102081473B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 발광 소자 | |
WO2018225943A1 (fr) | Nouveau composé et élément électroluminescent organique l'utilisant | |
KR102316570B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
JP2017533884A (ja) | 含窒素多環化合物及びこれを用いる有機発光素子 | |
JP6638924B2 (ja) | ヘテロ環化合物およびこれを用いた有機発光素子 | |
JP2017521366A (ja) | 複素環化合物及びこれを含む有機発光素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 17884616 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 17884616 Country of ref document: EP Kind code of ref document: A1 |