WO2013009079A1 - Composé à base de triphénylène et diode électroluminescente organique l'utilisant - Google Patents
Composé à base de triphénylène et diode électroluminescente organique l'utilisant Download PDFInfo
- Publication number
- WO2013009079A1 WO2013009079A1 PCT/KR2012/005474 KR2012005474W WO2013009079A1 WO 2013009079 A1 WO2013009079 A1 WO 2013009079A1 KR 2012005474 W KR2012005474 W KR 2012005474W WO 2013009079 A1 WO2013009079 A1 WO 2013009079A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- organic
- compound
- mmol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 97
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 title description 17
- 125000005580 triphenylene group Chemical group 0.000 title description 17
- 239000000463 material Substances 0.000 claims abstract description 48
- 239000010410 layer Substances 0.000 claims description 60
- 230000005525 hole transport Effects 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000011368 organic material Substances 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005104 aryl silyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 69
- 238000003786 synthesis reaction Methods 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- LEQPUUBCWZNYOX-UHFFFAOYSA-N S1C2=CC=CC=C2C2=C1C=C1C3=CC=C(Br)C=C3C3=CC=CC=C3C1=C2 Chemical compound S1C2=CC=CC=C2C2=C1C=C1C3=CC=C(Br)C=C3C3=CC=CC=C3C1=C2 LEQPUUBCWZNYOX-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 0 CC(*)c(c(*)c(c1c(C)c(C)c(*)c(*2)c1c(c1c3*)c2c(-c2c(C)c(*)c(*)c(*)c2C)c3N)c1c1*)c1O Chemical compound CC(*)c(c(*)c(c1c(C)c(C)c(*)c(*2)c1c(c1c3*)c2c(-c2c(C)c(*)c(*)c(*)c2C)c3N)c1c1*)c1O 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 metal complex compounds Chemical class 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 4
- BIVXRANYFMIUPE-UHFFFAOYSA-N (7-bromotriphenylen-2-yl)boronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=C(Br)C=C3C2=C1 BIVXRANYFMIUPE-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- NXLBFYUFQMPGPR-UHFFFAOYSA-N BrC1=CC=C2C=3C=CC(=CC3C3=CC=CC=C3C2=C1)C1=C(C=CC=C1)[SiH](C)C Chemical compound BrC1=CC=C2C=3C=CC(=CC3C3=CC=CC=C3C2=C1)C1=C(C=CC=C1)[SiH](C)C NXLBFYUFQMPGPR-UHFFFAOYSA-N 0.000 description 3
- GGGRXIVTLQEGLO-UHFFFAOYSA-N C=1C(Br)=CC=C(C2=CC3=C45)C=1C1=CC=CC=C1C2=CC3=CC4=CC=CC5(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical group C=1C(Br)=CC=C(C2=CC3=C45)C=1C1=CC=CC=C1C2=CC3=CC4=CC=CC5(C=1C=CC=CC=1)C1=CC=CC=C1 GGGRXIVTLQEGLO-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000002904 solvent Substances 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
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-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
- ZPEZHXMJCXCGLD-UHFFFAOYSA-N BrC1=CC=C2C3=CC4=C5C(C)(C)C=CC=C5C=C4C=C3C3=CC=CC=C3C2=C1 Chemical group BrC1=CC=C2C3=CC4=C5C(C)(C)C=CC=C5C=C4C=C3C3=CC=CC=C3C2=C1 ZPEZHXMJCXCGLD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- YGDICLRMNDWZAK-UHFFFAOYSA-N quinolin-3-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CN=C21 YGDICLRMNDWZAK-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- KOSBLTLSXQZTBI-UHFFFAOYSA-N (2-bromophenyl)-dimethylsilane Chemical compound C[SiH](C)C1=CC=CC=C1Br KOSBLTLSXQZTBI-UHFFFAOYSA-N 0.000 description 1
- LCWSTIIUVDKJGF-UHFFFAOYSA-N (4,6-dipyridin-4-ylpyrimidin-2-yl)boronic acid Chemical compound N=1C(B(O)O)=NC(C=2C=CN=CC=2)=CC=1C1=CC=NC=C1 LCWSTIIUVDKJGF-UHFFFAOYSA-N 0.000 description 1
- QPNHCOAFPUMKJU-UHFFFAOYSA-N (6-pyridin-3-ylpyridin-2-yl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=NC=CC=2)=N1 QPNHCOAFPUMKJU-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- NNNHMHLNXXGWBA-UHFFFAOYSA-N 1-bromo-2-methylsulfinylbenzene Chemical compound CS(=O)C1=CC=CC=C1Br NNNHMHLNXXGWBA-UHFFFAOYSA-N 0.000 description 1
- LECYCYNAEJDSIL-UHFFFAOYSA-N 1-bromo-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1Br LECYCYNAEJDSIL-UHFFFAOYSA-N 0.000 description 1
- UMQXTNDIXWKMGX-UHFFFAOYSA-N 2-(7-bromotriphenylen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC(Br)=CC=2)C=2C3=CC=CC=2)C3=C1 UMQXTNDIXWKMGX-UHFFFAOYSA-N 0.000 description 1
- XDGCDTURLQGEQU-UHFFFAOYSA-N 2-bromo-7-(2-methylsulfinylphenyl)triphenylene Chemical group CS(=O)C1=CC=CC=C1C1=CC=C(C=2C(=CC(Br)=CC=2)C=2C3=CC=CC=2)C3=C1 XDGCDTURLQGEQU-UHFFFAOYSA-N 0.000 description 1
- CCCUUGXUHRMQRK-UHFFFAOYSA-N 2-bromo-7-(2-propan-2-ylphenyl)triphenylene Chemical group CC(C)C1=CC=CC=C1C1=CC=C(C=2C(=CC(Br)=CC=2)C=2C3=CC=CC=2)C3=C1 CCCUUGXUHRMQRK-UHFFFAOYSA-N 0.000 description 1
- JDXVGZSASFWBJH-UHFFFAOYSA-N C(C1)C=Cc2c1[o]c1c2cc(c2ccccc2c2cc(-c3cc(cccc4)c4cc3)ccc22)c2c1 Chemical compound C(C1)C=Cc2c1[o]c1c2cc(c2ccccc2c2cc(-c3cc(cccc4)c4cc3)ccc22)c2c1 JDXVGZSASFWBJH-UHFFFAOYSA-N 0.000 description 1
- WQNOUIKKXXCUEG-UHFFFAOYSA-N CCC1C(C=CCC2)=C2c2ccccc12 Chemical compound CCC1C(C=CCC2)=C2c2ccccc12 WQNOUIKKXXCUEG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PBSIVXAPTBHFFV-UHFFFAOYSA-N [4-(1-phenylbenzimidazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 PBSIVXAPTBHFFV-UHFFFAOYSA-N 0.000 description 1
- BJNCAGKQHGBUJO-UHFFFAOYSA-N [4-(n-naphthalen-1-ylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 BJNCAGKQHGBUJO-UHFFFAOYSA-N 0.000 description 1
- XHSZIHPJXFLGIG-UHFFFAOYSA-N [4-(n-naphthalen-2-ylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XHSZIHPJXFLGIG-UHFFFAOYSA-N 0.000 description 1
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SBMXAWJSNIAHFR-UHFFFAOYSA-N n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC=3C=C4C=CC=CC4=CC=3)=CC=C21 SBMXAWJSNIAHFR-UHFFFAOYSA-N 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 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
- 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
- C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
-
- 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
-
- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Definitions
- the present invention relates to a triphenylene-based organic electroluminescent device material having a specific structure and to the organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the material in at least one organic material layer It is about.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
- the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
- a host / dopant system may be used as a light emitting material.
- Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Since the luminous efficiency can be improved up to 4 times compared to the phosphorescent dopant, a lot of research on phosphorescent host materials has been conducted.
- NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
- phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials.
- CBP is a phosphorescent host material and has shown high characteristics to date.
- existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and thermal stability is not very good, and thus it is not satisfactory in terms of lifespan in OLED devices. Therefore, the development of more excellent materials is required.
- the present invention has been made to solve the above problems, and an object thereof is to provide a novel organic compound having an improved glass transition temperature and excellent thermal stability.
- an object of the present invention is to provide an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, power efficiency, thermal stability, driving voltage, device life, including the novel organic compound.
- the present invention provides a compound represented by the following formula (1), preferably a triphenylene series organic electroluminescent device material.
- X is selected from the group consisting of CR 16 R 17 , O, S, SiR 18 R 19 , S ( ⁇ O), and S ( ⁇ O) 2 ;
- R 1 to R 19 are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 1 ⁇ C 40 alkoxy group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyl Amino group, C 6 ⁇ C 40 arylamino group, C 6 ⁇ C 40 diarylamino group, C 5 ⁇ C 40 heteroarylamino group, C 5 ⁇ C 40 diheteroarylamino group, C 6 ⁇ C 40 arylalkyl group , C 5 to C 40 heteroarylalkyl group, C 3 to C 40 cycloalkyl group, C 1 to C 40 halogenalkyl group, C 3 to C 40 heterocycl
- R 1 to R 19 may each be fused to an adjacent substituent or may form a ring.
- the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, a compound represented by the formula (1) It provides an organic electroluminescent device comprising at least one compound selected from the group consisting of.
- the organic material layer including the compound represented by Chemical Formula 1 may be at least one selected from the group consisting of a light emitting layer, a hole injection layer, and a hole transporting layer, and more preferably, a phosphorescent or fluorescent host material of the light emitting layer.
- Compound represented by the formula (1) of the present invention is excellent in brightness, power efficiency, heat resistance, hole or electron transport, injection performance, and can exhibit an increase in color purity and luminous efficiency to the light emitting layer, it is a hole and charge injection of the organic EL device It can be applied to at least one of a host, a dopant of phosphorescence and fluorescence of the layer, the transport layer and the light emitting layer.
- OLED organic electroluminescent device
- FIG. 1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.
- NPB N4, N4′-di (naphthalene-1-yl) -N4, N4′-diphenylbiphenyl-4,4′-diamine
- CBP 4,4- dicarbazolybiphenyl
- the compound represented by Formula 1 has an effect of stably forming triplet energy levels through orbital mixing by connecting a fused heterocyclic moiety to a triphenylene base skeleton.
- the energy level is controlled by a variety of substituents to have a wide bandgap (sky blue ⁇ red).
- the phosphorescence property of the device may be improved, and the electron and / or hole transport ability, the luminous efficiency, the driving voltage, and the lifespan characteristics may be improved. Therefore, the present invention may be applied to a hole transport layer, an electron transport layer, a host, and the like by introducing various substituents as well as the light emitting layer.
- the wide bandgap derived from the triphenylene base skeleton may exhibit excellent properties as a host material, and due to the introduction of substituents such as tertiary amines, it may exhibit excellent properties as a hole transport layer (HTL) material. have.
- HTL hole transport layer
- the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the triphenylene-based skeleton, so that the glass transition temperature is improved, which may have higher thermal stability than conventional NPB or CBP. have. Therefore, the device containing the triphenylene-based compound of the present invention can exhibit durability and lifespan improvement.
- the compound represented by the compound of Formula 1 according to the present invention can greatly contribute to the performance improvement and lifespan improvement of the organic light emitting device, and in particular, the device life improvement has a great effect on maximizing performance in the full color organic light emitting panel.
- R 1 to R 19 are the same as defined in Chemical Formula 1.
- the compound of formula (I) including S as X may be more specified by the formulas illustrated below.
- the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
- the compound of the formula (1) comprising O as X may be more specified by the formulas illustrated below.
- the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
- the compound of formula (I) comprising CR 16 R 17 as X may be more specified by the formulas illustrated below.
- the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
- the compound of formula 1 comprising SiR 18 R 19 as X may be more embodied by the formulas illustrated below.
- the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
- the compound of formula (I) including S ⁇ O as X may be more specified by the formulas illustrated below.
- the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
- the compound of formula (I) comprising SO 2 as X may be more specified by the formulas illustrated below.
- the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
- the compounds represented by Formulas 1 to 7 of the present invention may be synthesized according to a general synthesis method. (see chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995)) A detailed synthesis procedure for the compounds of the present invention is described This will be described in detail.
- Another aspect of the invention relates to an organic electroluminescent device comprising a compound represented by Formula 1, preferably Formula 2 to Formula 7, according to the present invention described above.
- the present invention is an anode (anode); Cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer is represented by Formula 1, preferably, Formulas 2 to 7. It is characterized by including a compound.
- the compound of Formula 1 to Formula 7 may be included alone or in plurality.
- the organic material layer including the compound represented by Chemical Formula 1, preferably Chemical Formulas 2 to 7, may be any one or more of a hole injection layer, a hole transport layer, and a light emitting layer.
- it can be included in the organic EL element as a hole injection layer and a hole transport layer material.
- the organic EL device can maximize the hole injection / transport ability.
- by being used as a light emitting layer material of an organic EL device it is possible to provide improved efficiency and lifetime.
- the light emitting layer may include a phosphorescent guest material or a fluorescent guest material.
- the compound represented by Formula 1 to Formula 7 may be included in the organic light emitting device as a blue, green and / or red phosphorescent host, a fluorescent host, a hole transport material and / or a hole transport material.
- the triphenylene compound according to the present invention is preferable as a host material.
- Compounds of formula (1) into which substituents such as tertiary amines are introduced are preferred as hole transport layer (HTL) materials.
- the compound represented by Formula 1, preferably, Formulas 2 to 7, according to the present invention has a high glass transition temperature of 150 °C or more. Therefore, when the compound is used as an organic material layer of the organic light emitting device, since crystallization in the organic light emitting device is minimized, the driving voltage of the device can be lowered, and the luminous efficiency, thermal stability, and lifespan characteristics can be improved.
- a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked.
- at least one of the emission layer, the hole injection layer, and the hole transport layer may include the compound represented by Chemical Formula 1.
- An electron injection layer may be positioned on the electron transport layer.
- the organic light emitting device may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic layer.
- the organic layer including the compound of Formula 1 to Formula 7 may be formed by a vacuum deposition method or a solution coating method.
- the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
- the organic electroluminescent device according to the present invention is an organic material layer and an electrode using conventional materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1 above. It can be prepared by forming.
- a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
- the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
- Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the hole injection layer, the hole transport layer and the electron injection layer is not particularly limited, and conventional materials known in the art may be used.
- An organic EL device was manufactured in the following manner.
- the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- ITO Indium tin oxide
- the light emitting device was NPB (40 nm) / CBP + 10% Ir (ppy) 3 (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF (1 nm) / Al. After the configuration, the luminescence properties were evaluated in the same manner as in Examples 1 to 11.
- NPB, CBP, Ir (ppy) 3 and BCP are as follows.
- An organic EL device was manufactured in the following manner.
- the glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Cette invention concerne un nouveau composé électroluminescent organique et une diode électroluminescente organique le contenant, et plus particulièrement, un nouveau composé électroluminescent organique qui est utilisé à titre de matériau pour injecter et transférer des trous ou des électrons et émettre une lumière, et une diode électroluminescente organique l'utilisant.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2011-0068609 | 2011-07-11 | ||
KR1020110068609A KR101470055B1 (ko) | 2011-07-11 | 2011-07-11 | 트리페닐렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013009079A1 true WO2013009079A1 (fr) | 2013-01-17 |
Family
ID=47506265
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2012/005474 WO2013009079A1 (fr) | 2011-07-11 | 2012-07-11 | Composé à base de triphénylène et diode électroluminescente organique l'utilisant |
Country Status (2)
Country | Link |
---|---|
KR (1) | KR101470055B1 (fr) |
WO (1) | WO2013009079A1 (fr) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014094954A1 (fr) * | 2012-12-18 | 2014-06-26 | Merck Patent Gmbh | Composés à base d'indénophénanthrène |
US20160190472A1 (en) * | 2014-12-30 | 2016-06-30 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
CN105801430A (zh) * | 2015-01-19 | 2016-07-27 | 机光科技股份有限公司 | 菲并[9,10-b]联亚四苯衍生物以及其用途 |
JP2016525512A (ja) * | 2013-07-10 | 2016-08-25 | サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. | 有機化合物、有機光電子素子および表示装置 |
JP2016153394A (ja) * | 2015-02-17 | 2016-08-25 | 機光科技股▲分▼有限公司 | 有機エレクトロルミネセンス素子用インデノトリフェニレン系アミン誘導体 |
US20170012211A1 (en) * | 2015-07-10 | 2017-01-12 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN106831622A (zh) * | 2015-12-03 | 2017-06-13 | 机光科技股份有限公司 | 有机材料及使用其的有机电激发光组件 |
CN106986813A (zh) * | 2016-01-06 | 2017-07-28 | 机光科技股份有限公司 | 用于有机电场发光装置的基于茚并三亚苯的胺衍生物 |
TWI619690B (zh) * | 2015-11-23 | 2018-04-01 | 機光科技股份有限公司 | 有機化合物及使用其的有機電激發光元件 |
US10164194B2 (en) * | 2015-01-26 | 2018-12-25 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
CN110526825A (zh) * | 2018-05-25 | 2019-12-03 | 江苏三月光电科技有限公司 | 一种以异屈与三芳胺结构为核心的化合物及其应用 |
CN110546143A (zh) * | 2017-07-10 | 2019-12-06 | 株式会社Lg化学 | 新型杂环化合物及包含其的有机发光器件 |
CN111320607A (zh) * | 2018-12-17 | 2020-06-23 | 机光科技股份有限公司 | 以含有三亚苯的多环杂芳族基团为核心的有机化合物及其应用 |
US10807972B2 (en) | 2018-10-15 | 2020-10-20 | Feng-wen Yen | Indenotriphenylene-based amine derivative and organic electroluminescence device using the same |
CN112961140A (zh) * | 2021-02-08 | 2021-06-15 | 北京云基科技有限公司 | 一种萘醌杂环化合物及应用 |
CN113004243A (zh) * | 2021-02-08 | 2021-06-22 | 北京云基科技有限公司 | 一种含萘醌的杂环化合物及其应用 |
CN113004261A (zh) * | 2021-02-08 | 2021-06-22 | 北京云基科技有限公司 | 一种含多杂环结构的化合物及其应用 |
CN113004262A (zh) * | 2021-02-08 | 2021-06-22 | 北京云基科技有限公司 | 一种有机材料及其应用 |
US11177446B2 (en) * | 2017-09-14 | 2021-11-16 | Beijing Summer Sprout Technology Co., Ltd. | Silicon containing organic fluorescent materials |
TWI747141B (zh) * | 2019-01-17 | 2021-11-21 | 機光科技股份有限公司 | 有機化合物及使用其的有機電致發光器件 |
TWI792166B (zh) * | 2021-01-29 | 2023-02-11 | 機光科技股份有限公司 | 有機化合物和以其作為材料的紅光有機發光裝置 |
CN116003356A (zh) * | 2022-12-30 | 2023-04-25 | 宁波卢米蓝新材料有限公司 | 含有三亚苯的多环杂芳族基团的化合物及其有机电致发光材料及其应用 |
CN116655653A (zh) * | 2023-05-06 | 2023-08-29 | 南昌航空大学 | 一种新型扭曲砜类多功能分子的制备及其应用 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102078365B1 (ko) | 2013-07-01 | 2020-04-03 | 삼성디스플레이 주식회사 | 유기 발광 장치 |
KR102253441B1 (ko) | 2014-03-10 | 2021-05-20 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
KR101503796B1 (ko) * | 2014-05-08 | 2015-03-18 | 성균관대학교산학협력단 | 유기 발광 화합물, 이의 제조 방법 및 이를 포함하는 유기 전계 발광 소자 |
KR101904299B1 (ko) | 2014-05-12 | 2018-10-04 | 제일모직 주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
US10312451B2 (en) * | 2015-01-26 | 2019-06-04 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
KR102018238B1 (ko) | 2016-09-21 | 2019-09-04 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
KR101962756B1 (ko) | 2016-09-29 | 2019-03-27 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
WO2019013509A1 (fr) * | 2017-07-10 | 2019-01-17 | 주식회사 엘지화학 | Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant |
CN111087416B (zh) * | 2018-10-24 | 2024-05-14 | 北京夏禾科技有限公司 | 含硅的电子传输材料及其应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006130598A2 (fr) * | 2005-05-31 | 2006-12-07 | Universal Display Corporation | Hotes de triphenylene dans des diodes luminescentes phosphorescentes |
WO2009037155A1 (fr) * | 2007-09-20 | 2009-03-26 | Basf Se | Dispositif électroluminescent |
JP2009114068A (ja) * | 2007-11-01 | 2009-05-28 | Canon Inc | トリフェニレン化合物及びこれを用いた有機発光素子 |
KR101023623B1 (ko) * | 2008-10-24 | 2011-03-22 | 주식회사 이엘엠 | 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자 |
KR20120072784A (ko) * | 2010-12-24 | 2012-07-04 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI448534B (zh) * | 2009-09-28 | 2014-08-11 | Ritdisplay Corp | 有機電致發光元件 |
-
2011
- 2011-07-11 KR KR1020110068609A patent/KR101470055B1/ko active IP Right Grant
-
2012
- 2012-07-11 WO PCT/KR2012/005474 patent/WO2013009079A1/fr active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006130598A2 (fr) * | 2005-05-31 | 2006-12-07 | Universal Display Corporation | Hotes de triphenylene dans des diodes luminescentes phosphorescentes |
WO2009037155A1 (fr) * | 2007-09-20 | 2009-03-26 | Basf Se | Dispositif électroluminescent |
JP2009114068A (ja) * | 2007-11-01 | 2009-05-28 | Canon Inc | トリフェニレン化合物及びこれを用いた有機発光素子 |
KR101023623B1 (ko) * | 2008-10-24 | 2011-03-22 | 주식회사 이엘엠 | 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자 |
KR20120072784A (ko) * | 2010-12-24 | 2012-07-04 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
Cited By (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014094954A1 (fr) * | 2012-12-18 | 2014-06-26 | Merck Patent Gmbh | Composés à base d'indénophénanthrène |
US10032990B2 (en) | 2013-07-10 | 2018-07-24 | Samsung Sdi Co., Ltd. | Organic composition, and organic optoelectronic element and display device |
JP2016525512A (ja) * | 2013-07-10 | 2016-08-25 | サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. | 有機化合物、有機光電子素子および表示装置 |
US20160190472A1 (en) * | 2014-12-30 | 2016-06-30 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
CN105732594A (zh) * | 2014-12-30 | 2016-07-06 | 机光科技股份有限公司 | 有机材料和使用其的有机电致发光装置 |
JP2016155797A (ja) * | 2014-12-30 | 2016-09-01 | 機光科技股▲分▼有限公司 | 有機材料およびそれを用いた有機エレクトロルミネッセンス素子 |
TWI564290B (zh) * | 2014-12-30 | 2017-01-01 | 機光科技股份有限公司 | 有機材料及使用此材料之有機電激發光裝置 |
US9793493B2 (en) * | 2014-12-30 | 2017-10-17 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
CN105801430A (zh) * | 2015-01-19 | 2016-07-27 | 机光科技股份有限公司 | 菲并[9,10-b]联亚四苯衍生物以及其用途 |
CN105801430B (zh) * | 2015-01-19 | 2018-08-28 | 机光科技股份有限公司 | 菲并[9,10-b]联亚四苯衍生物以及其用途 |
US10164194B2 (en) * | 2015-01-26 | 2018-12-25 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
JP2016153394A (ja) * | 2015-02-17 | 2016-08-25 | 機光科技股▲分▼有限公司 | 有機エレクトロルミネセンス素子用インデノトリフェニレン系アミン誘導体 |
US20170012211A1 (en) * | 2015-07-10 | 2017-01-12 | Samsung Display Co., Ltd. | Organic light-emitting device |
TWI619690B (zh) * | 2015-11-23 | 2018-04-01 | 機光科技股份有限公司 | 有機化合物及使用其的有機電激發光元件 |
TWI617547B (zh) * | 2015-12-03 | 2018-03-11 | Luminescence Technology Corporation | 有機材料及使用其的有機電激發光元件 |
CN106831622A (zh) * | 2015-12-03 | 2017-06-13 | 机光科技股份有限公司 | 有机材料及使用其的有机电激发光组件 |
CN106986813A (zh) * | 2016-01-06 | 2017-07-28 | 机光科技股份有限公司 | 用于有机电场发光装置的基于茚并三亚苯的胺衍生物 |
CN110546143A (zh) * | 2017-07-10 | 2019-12-06 | 株式会社Lg化学 | 新型杂环化合物及包含其的有机发光器件 |
US11177446B2 (en) * | 2017-09-14 | 2021-11-16 | Beijing Summer Sprout Technology Co., Ltd. | Silicon containing organic fluorescent materials |
CN110526825B (zh) * | 2018-05-25 | 2023-04-07 | 江苏三月科技股份有限公司 | 一种以异屈与三芳胺结构为核心的化合物及其应用 |
CN110526825A (zh) * | 2018-05-25 | 2019-12-03 | 江苏三月光电科技有限公司 | 一种以异屈与三芳胺结构为核心的化合物及其应用 |
US10807972B2 (en) | 2018-10-15 | 2020-10-20 | Feng-wen Yen | Indenotriphenylene-based amine derivative and organic electroluminescence device using the same |
TWI728502B (zh) * | 2018-10-15 | 2021-05-21 | 機光科技股份有限公司 | 基於茚並三亞苯的胺衍生物及使用其的有機電激發光裝置 |
CN111320607A (zh) * | 2018-12-17 | 2020-06-23 | 机光科技股份有限公司 | 以含有三亚苯的多环杂芳族基团为核心的有机化合物及其应用 |
TWI783194B (zh) * | 2018-12-17 | 2022-11-11 | 機光科技股份有限公司 | 以含有三亞苯的多環雜芳族基團為核心的有機化合物及其應用 |
CN111320607B (zh) * | 2018-12-17 | 2021-11-19 | 机光科技股份有限公司 | 以含有三亚苯的多环杂芳族基团为核心的有机化合物及其应用 |
TWI747141B (zh) * | 2019-01-17 | 2021-11-21 | 機光科技股份有限公司 | 有機化合物及使用其的有機電致發光器件 |
TWI792166B (zh) * | 2021-01-29 | 2023-02-11 | 機光科技股份有限公司 | 有機化合物和以其作為材料的紅光有機發光裝置 |
CN113004243A (zh) * | 2021-02-08 | 2021-06-22 | 北京云基科技有限公司 | 一种含萘醌的杂环化合物及其应用 |
CN113004262A (zh) * | 2021-02-08 | 2021-06-22 | 北京云基科技有限公司 | 一种有机材料及其应用 |
CN113004261A (zh) * | 2021-02-08 | 2021-06-22 | 北京云基科技有限公司 | 一种含多杂环结构的化合物及其应用 |
CN112961140B (zh) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | 一种萘醌杂环化合物及应用 |
CN113004261B (zh) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | 一种含多杂环结构的化合物及其应用 |
CN113004243B (zh) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | 一种含萘醌的杂环化合物及其应用 |
CN113004262B (zh) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | 一种有机材料及其应用 |
CN112961140A (zh) * | 2021-02-08 | 2021-06-15 | 北京云基科技有限公司 | 一种萘醌杂环化合物及应用 |
CN116003356A (zh) * | 2022-12-30 | 2023-04-25 | 宁波卢米蓝新材料有限公司 | 含有三亚苯的多环杂芳族基团的化合物及其有机电致发光材料及其应用 |
CN116655653A (zh) * | 2023-05-06 | 2023-08-29 | 南昌航空大学 | 一种新型扭曲砜类多功能分子的制备及其应用 |
Also Published As
Publication number | Publication date |
---|---|
KR20130007934A (ko) | 2013-01-21 |
KR101470055B1 (ko) | 2014-12-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2013009079A1 (fr) | Composé à base de triphénylène et diode électroluminescente organique l'utilisant | |
WO2020027389A1 (fr) | Composé électroluminescent organique et élément électroluminescent organique le comprenant | |
WO2019124902A1 (fr) | Élément électronique organique utilisant un composé d'élément électronique organique et dispositif électronique associé | |
WO2014142472A1 (fr) | Composé pour élément électrique organique, élément électrique organique utilisant celui-ci, et dispositif électronique associé | |
WO2011149240A2 (fr) | Composé à base de triphénylène bipolaire et élément électroluminescent organique le comprenant | |
WO2013051875A2 (fr) | Dispositif électroluminescent organique et son procédé de fabrication | |
WO2011081429A2 (fr) | Composé organique et dispositif électroluminescent organique l'utilisant | |
WO2011139125A2 (fr) | Composé de phénanthrocarbazole, et dispositif électroluminescent organique utilisant ce composé | |
WO2014003336A1 (fr) | Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé | |
WO2010131930A2 (fr) | Composé pour dispositif photoélectrique organique et dispositif photoélectrique organique comprenant ce composé | |
WO2011037429A2 (fr) | Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique | |
WO2012099376A2 (fr) | Nouveau composé et dispositif électroluminescent organique comprenant ledit composé | |
WO2011149283A2 (fr) | Composé comprenant un hétérocycle à cinq chaînons, élément électrique organique l'utilisant et borne correspondante | |
WO2011081431A2 (fr) | Composé émetteur de lumière organique, et dispositif électroluminescent organique l'utilisant | |
WO2011059271A2 (fr) | Nouveau composé comprenant un anneau condensé, et dispositif électronique organique qui utilise celui-ci | |
WO2011139129A2 (fr) | Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant | |
WO2015080404A1 (fr) | Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant | |
WO2011108901A9 (fr) | Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci | |
WO2014123369A1 (fr) | Nouveau composé et élément électronique organique l'utilisant | |
WO2018169261A1 (fr) | Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé | |
WO2014098455A1 (fr) | Nouveau composé organique et élément électroluminescent organique le comprenant | |
WO2017014460A1 (fr) | Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé | |
WO2021045444A1 (fr) | Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé | |
WO2016013817A2 (fr) | Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant | |
WO2014084612A1 (fr) | Nouveau composé et élément électronique organique l'utilisant |
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: 12811055 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
32PN | Ep: public notification in the ep bulletin as address of the adressee cannot be established |
Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 02-05-2014 ) |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 12811055 Country of ref document: EP Kind code of ref document: A1 |