CN112400007A - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
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- CN112400007A CN112400007A CN201980045174.0A CN201980045174A CN112400007A CN 112400007 A CN112400007 A CN 112400007A CN 201980045174 A CN201980045174 A CN 201980045174A CN 112400007 A CN112400007 A CN 112400007A
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- substituted
- unsubstituted
- group
- alkyl
- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 85
- -1 cyano, carboxyl Chemical group 0.000 claims description 179
- 239000000463 material Substances 0.000 claims description 48
- 230000005525 hole transport Effects 0.000 claims description 44
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000005104 aryl silyl group Chemical group 0.000 claims description 27
- 125000001769 aryl amino group Chemical group 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 239000010410 layer Substances 0.000 description 109
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 229910052732 germanium Inorganic materials 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002096 quantum dot Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- OWPJBAYCIXEHFA-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 OWPJBAYCIXEHFA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NUGMENVSVAURGO-UHFFFAOYSA-N 2-bromo-6-chlorobenzaldehyde Chemical compound ClC1=CC=CC(Br)=C1C=O NUGMENVSVAURGO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OBARUOOPPWHZRQ-UHFFFAOYSA-N 9,9-dimethyl-n-(2-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC1=CC=CC=C1C1=CC=CC=C1 OBARUOOPPWHZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZHVOQKHZCNGWET-UHFFFAOYSA-N N,9-diphenylcarbazol-2-amine Chemical compound C1(=CC=CC=C1)NC1=CC=2N(C3=CC=CC=C3C2C=C1)C1=CC=CC=C1 ZHVOQKHZCNGWET-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005870 benzindolyl group Chemical group 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group 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
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 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
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FTMRMQALUDDFQO-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran Chemical group C1=CC=C2C=C3C4=CC=CC=C4OC3=CC2=C1 FTMRMQALUDDFQO-UHFFFAOYSA-N 0.000 description 1
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical group C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010189 synthetic method 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
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
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- 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
- C07D333/76—Dibenzothiophenes
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- C07D409/12—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 linked by a chain containing hetero atoms as chain links
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
The present disclosure relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the same. By including the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having a low driving voltage and/or high luminous efficiency and a long life can be provided, compared to a conventional organic electroluminescent device.
Description
Technical Field
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
Background
TPD/Alq with green emission consisting of a light-emitting layer and a charge transport layer3Bilayer small molecule organic electroluminescent devices were first developed by Tang et al, Eastman Kodak, Ischman Kodak in 1987. Since then, research on organic electroluminescent devices is rapidly commercialized. An organic electroluminescent device (OLED) converts electrical energy into light by applying power to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic electroluminescent device has a multi-layered structure including a hole transport region, a light emitting layer, an electron transport region, and the like, to improve efficiency and stability thereof.
In addition, research into new compounds capable of improving the performance of the organic electroluminescent device has been actively conducted, because the performance of the organic electroluminescent device largely depends on the compounds contained in each region or a layer thereof. For example, copper phthalocyanine (CuPc), 4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N' -diphenyl-N, N '-bis (3-methylphenyl) - (1, 1' -biphenyl) -4,4 '-diamine (TPD), 4', 4 ″ -tris (3-methylphenylphenylamino) triphenylamine (MTDATA), and the like are used as compounds contained in the hole transport region in the organic electroluminescent device. However, organic electroluminescent devices using these materials have problems of reduced luminous efficiency and lifetime. This is because, when the organic electroluminescent device is driven at a high current, thermal stress occurs between the anode and the hole injection layer, and thus such thermal stress significantly reduces the lifetime of the device. In addition, since the organic material used in the hole transport region has very high hole mobility, there are problems in that hole-electron charge balance is disrupted and quantum efficiency (cd/a) is lowered. Therefore, new compounds capable of replacing conventional compounds used in the hole transport region are required. In addition, research into various materials and devices for improving light emitting efficiency, driving voltage, and/or life span characteristics of the organic electroluminescent device has been conducted.
KR 2017-0096770A discloses only a compound in which an amine is bonded to a specific position of benzonaphthothiophene or benzonaphthofuran as a compound contained in a hole transport layer of an organic electroluminescent device.
Disclosure of Invention
Technical problem
An object of the present disclosure is to provide an organic electroluminescent compound effective for producing an organic electroluminescent device having a low driving voltage and/or a high luminous efficiency and/or a long life.
Solution to the problem
The present inventors found that the above object can be achieved due to an organic electroluminescent compound represented by the following formula 1, which reduces the degree of free rotation and increases the rigidity of the molecule by steric hindrance of the molecule without significantly changing the triplet energy as compared with the compound disclosed in KR 2017-0096770A, and then completed the present invention.
In the formula 1, the first and second groups,
x represents O or S;
Ar1to Ar4Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or Ar1And Ar2And Ar3And Ar4May be linked to each other to form a ring;
L1and L2Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
R1and R2Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C3)0) Cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;
a represents an integer of 1 to 4, b represents an integer of 1 to 5, and when a and b are 2 or more, R1Each of (1) and R2Each of which may be the same or different; and is
p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, and when the sum of p and q is 2, L1And L2And Ar1To Ar4May be the same or different.
The invention has the advantages of
The organic electroluminescent compounds according to the present disclosure may provide organic electroluminescent devices having a low driving voltage, high luminous efficiency, and/or a long lifetime.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention and is not meant to limit the scope of the invention in any way.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used for an organic electroluminescent device and can be contained in any material layer constituting the organic electroluminescent device if necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may include at least one compound. If necessary, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, or the like.
The term "hole transport region" means a region where holes move between the first electrode and the light emitting layer. For example, the hole transport region may include at least one of a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole assist layer, the light emission assist layer, and the electron blocking layer may each be a single layer or a multilayer in which two or more layers are stacked. According to one embodiment, the hole transport region may include a first hole transport layer and a second hole transport layer. The second hole transport layer may be at least one of a plurality of hole transport layers and include at least one of a hole assist layer, a light emission assist layer, and/or an electron blocking layer. Further, according to another embodiment, the hole transport region may include a first hole transport layer and a second hole transport layer. The first hole transport layer may be interposed between the first electrode and the light emitting layer, and the second hole transport layer may be interposed between the first hole transport layer and the light emitting layer. The second hole transport layer may function as a hole transport layer, a light emission assisting layer, a hole assisting layer and/or an electron blocking layer.
The hole transport layer may be interposed between the anode (or the hole injection layer) and the light emitting layer, and may serve to smoothly move holes transferred from the anode to the light emitting layer and block electrons transferred from the cathode to remain in the light emitting layer. The light-emitting auxiliary layer may be disposed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is interposed between the anode and the light-emitting layer, it may be used to facilitate hole injection and/or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is interposed between the cathode and the light-emitting layer, it may be used to facilitate electron injection and/or electron transport, or to prevent hole overflow. In addition, a hole assist layer may be interposed between the hole transport layer (or hole injection layer) and the light emitting layer, and the hole transport rate (or hole injection rate) may be effectively promoted or limited, thereby enabling control of charge balance.
In addition, an electron blocking layer may be interposed between the hole transport layer (or the hole injection layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking the overflow of electrons from the light emitting layer to prevent light emission leakage. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layers further included may be used as a light emission auxiliary layer, a hole auxiliary layer, an electron blocking layer, and the like. The light-emitting auxiliary layer, the hole auxiliary layer, and/or the electron blocking layer may have an effect of improving the light-emitting efficiency and/or lifetime of the organic electroluminescent device.
Herein, "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C2-C30) alkenyl" is a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. "(C2-C30) alkynyl" is a straight or branched chain alkynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. "(C3-C30) cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3-to 7-membered) heterocycloalkyl" is a cycloalkyl group having 3 to 7 ring backbone atoms, wherein the number of ring backbone atoms is preferably 5 to 7, including at least one heteroatom selected from the group consisting of B, N, O, S, Si and P (preferably, O, S and N). The above-mentioned heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, thiacyclopentane, tetrahydropyran, and the like. "(C6-C30) (arylene) is a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, andmay comprise a spiro structure. Examples of the aryl group specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthryl, benzanthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, binaphthyl, and the like,
Radical, benzo
Mesityl, naphthonaphthyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro [ fluorene-fluorene ]]Spiro [ fluorene-benzofluorene ] s]Mesityl, azulenyl, etc. More specifically, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesitylene, o-cumenyl, m-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4' -methylbiphenyl, 4 "-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-terphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, p-terphenyl-4-yl, p-terphenyl-, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-
Base 2-
Base 3-
Base, 4-
Base 5-
Base 6-
Radical, benzo [ c]Phenanthryl, benzo [ g ]]
A group such as a 1-triphenylene group, a 2-triphenylene group, a 3-triphenylene group, a 4-triphenylene group, a 3-fluoranthenyl group, a 4-fluoranthenyl group, an 8-fluoranthenyl group, a 9-fluoranthenyl group, or a benzofluoranthenyl group.
Herein, "(3-to 30-membered) (arylene) heteroaryl" is an aryl group having 3 to 30 ring backbone atoms, wherein the number of ring backbone atoms is preferably 5 to 25, including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P and Ge. The above-mentioned heteroaryl group may be a monocyclic ring, or a condensed ring condensed with at least one benzene ring; and may be partially saturated. The above-mentioned hetero atom may be bonded to at least one substituent selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, And substituted or unsubstituted (C1-C30) alkyl (C6-30) arylamino. In addition, the above-mentioned heteroaryl group may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds; and may comprise a spiro structure. Examples of the heteroaryl group may specifically include monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused ring heteroaryl groups including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl and the like, Azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, silafluorenyl, germanofluorenyl, and the like. More specifically, the heteroaryl group may be a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyrimidyl group, a 4-pyrimidyl group, a 5-pyrimidyl group, a 6-pyrimidyl group, a 1,2, 3-triazin-4-yl group, a 1,2, 4-triazin-3-yl group, a 1,3, 5-triazin-2-yl group, a 1-imidazolyl group, a 2-imidazolyl group, a 1-pyrazolyl group, a 1-indolizidinyl group, a 2-indolizidinyl group, a 3-indolizidinyl group, a 5-indolizidinyl group, a 6-indolizidinyl group, a 7-indolizidinyl group, an 8-indolizidinyl group, a 2-imidazopyridinyl group, a, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalyl group, 5-quinoxalyl group, 6-quinoxalyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazol-1-yl group, azacarbazol-2-yl group, a, Azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 2-phenanthridinyl, etc, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, and 4-germanium fluorenyl, and the like. "halogen" includes F, Cl, Br, and I.
Herein, "O (O)", "m (m)", and "p (p)" are intended to indicate the substitution positions of all substituents. The ortho positions are compounds having substituents adjacent to each other, for example at the 1 and 2 positions on benzene. The meta position is a substitution position next to the substitution position immediately, and for example, the compound has a substituent at the 1-position and the 3-position on benzene. The para position is the next substitution position of the meta position, and for example, the compound has substituents at the 1-and 4-positions on benzene.
Further, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or functional group (i.e., substituent). Substituted (C1-C30) alkyl, substituted (C6-C30) (arylene), substituted (3-to 30-membered) (arylene) heteroaryl, substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted tri (C1-C30) alkylsilyl, substituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted tri (C6-C30) arylsilyl, substituted mono-or di- (C1-C30) alkylamino, substituted mono-or di- (C6-C30) arylamino, and substituted (C1-C30) alkyl (C6-C30) arylamino substituents each independently being at least one selected from the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or unsubstituted (3-to 30-membered) heteroaryl, (3-to 30-membered) heteroaryl substituted or unsubstituted (C6-C30) aryl, tri (C1-C7) alkylsilyl, tri (C6-C30) arylsilyl, di (C30-C30) alkyl (C30-C30) arylsilyl, (C30-C36 30 2) arylsilyl, Amino, mono-or di- (C1-C30) alkylamino, (C1-C30) alkyl-substituted or unsubstituted mono-or di- (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylborarbonyl, di (C1-C30) alkylborarbonyl, (C1-C30) alkyl (C6-C30) arylborarbonyl, (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment, the substituents each independently represent a (C1-C20) alkyl group and/or a (C6-C25) aryl group. According to another embodiment, the substituents each independently represent at least one of a (C1-C10) alkyl group and a (C6-C18) aryl group. For example, each substituent may be, independently, at least one of methyl, phenyl, naphthyl, and biphenyl.
Herein, "a ring formed by connecting to adjacent substituents" means a substituted or unsubstituted (3-to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, formed by connecting or fusing two or more adjacent substituents; preferably, it may be a substituted or unsubstituted (3-to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof. In addition, the ring formed may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P (preferably, N, O and S).
In the formulae of the present disclosure, each of the heteroaryl (ene) group and the heterocycloalkyl group independently may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Ge. Further, the above-mentioned hetero atom may be bonded to at least one substituent selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, And substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino.
The compound represented by formula 1 may be represented by any one of the following formulae 2 to 4.
In formulae 2 to 4，X、Ar1To Ar4、L1、L2、R1、R2A, b, p and q are as defined in formula 1. According to one embodiment, the sum of p and q may be 1.
In formulae 1 to 4, X represents O or S.
In formulae 1 to 4, Ar1To Ar4Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or Ar1And Ar2May be linked to each other to form a ring, and Ar3And Ar4May be connected to each other to form a ring. According to one embodiment, Ar1To Ar4Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (3-to 25-membered) heteroaryl group, a substituted or unsubstituted mono-or di- (C1-C20) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C25) arylamino group, or a substituted or unsubstituted (C1-C20) alkyl (C6-C25) arylamino group. According to another embodiment, Ar1To Ar4Each independently represents a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group. For example, Ar1To Ar4Each independently can be an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, an unsubstituted phenanthryl group, an unsubstituted naphthylphenyl group, a phenyl substituted or unsubstituted dimethylfluorenyl group, an unsubstituted diphenylfluorenyl group, an unsubstituted terphenyl group, a spirobifluorenyl group, a phenyl substituted or unsubstituted dibenzothienyl group, a dibenzofuranyl group, or a carbazolyl group substituted with at least one phenyl group and/or substituted with at least one biphenyl group.
According to one embodiment, Ar1And Ar2Or Ar3And Ar4Each independently may be selected from the following groups. For example, when Ar1When is phenyl, Ar2Any of the following compounds may be used.
In formulae 1 to 4, L1And L2Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene; according to one embodiment, L1And L2Each of which isIndependently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-to 25-membered) heteroarylene; according to another embodiment, L1And L2Each independently represents a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (3-to 18-membered) heteroarylene. For example, L1And L2Each independently may be a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group.
In formulae 1 to 4, R1And R2Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; according to one embodiment, R1And R2Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-to 25-membered) heteroaryl; according to another embodiment, R1And R2Each independently represents hydrogen, deuterium, halogen, cyano, unsubstituted (C1-C10) alkyl, unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-to 25-membered) heteroaryl. For example, R1And R2May be hydrogen.
In formulae 1 to 4, a represents an integer of 1 to 4, b represents an integer of 1 to 5, and R is represented by R when a and b are each 2 or more1Each of (1) and R2Each of which may be the same or different; and according to one embodiment, a and b may be 1.
In formulae 1 to 4, p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, and when the sum of p and q is 2, each of the substituents may be the same or different; and according to one embodiment, the sum of p and q may be 1. For example, when p is 0, q is 1; and q is 0 when p is 1.
The compound represented by formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto.
The organic electroluminescent compounds of the present disclosure can be produced by synthetic methods known to those skilled in the art. For example, the organic electroluminescent compounds of the present disclosure may be synthesized as shown by the following reaction schemes 1 to 3, but are not limited thereto.
[ reaction scheme 1]
[ reaction scheme 2]
[ reaction scheme 3]
In reaction schemes 1 to 3, X, Ar1To Ar4、L1、L2、R1、R2A, b, p and q are as defined in formula 1.
As described above, exemplary synthetic examples of the compounds represented by formulae 2 to 4 according to one embodiment are described, but they are based on the Buchwald-hartwigh cross-coupling reaction, Wittig (Wittig) reaction, Ullmann-coupling reaction, Suzuki (Suzuki) cross-coupling reaction, N-arylation reaction, acidified montmorillonite (H-mont) -mediated etherification reaction, Miyaura's (Miyaura) boronization reaction, intramolecular acid-induced cyclization reaction, pd (ii) -catalyzed oxidative cyclization reaction, Grignard (Grignard) reaction, Heck (Heck) reaction, dehydration cyclization reaction, SN (llkur) reaction1Substitution reaction, SN2Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like. It will be appreciated by those skilled in the art that the above reaction proceeds even if other substituents defined in formulae 2 to 4 than those described in specific synthetic examples are bonded.
The dopant that may be used in combination with the compounds of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant is not particularly limited, but may be a complex compound of a metallized metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably a complex compound of an ortho-metallized metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
The dopant may use a compound represented by any one of the following formulae 101 to 103, but is not limited thereto:
wherein L is selected from the following structures 1 or 2:
R100each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group;
R101to R109And R111To R123Each independently represents hydrogen, deuterium, halogen, deuterium substituted or halogen substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to an adjacent substituent to form a ring; specifically, R106To R109May be linked to an adjacent substituent to form a ring, for example, an alkyl substituted or unsubstituted indene ring, an alkyl substituted or unsubstituted benzothiophene ring, or an alkyl substituted or unsubstituted benzofuran ring; r120To R123May be linked to an adjacent substituent to form a ring, e.g. R120And R121May be linked to each other to form at least one of an alkyl-, aryl-, aralkyl-, and alkaryl-substituted or unsubstituted benzene ring, or at least one alkyl-substituted or unsubstituted fluorene ring, dibenzofuran ring, or dibenzothiophene ring;
R124to R127Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; or may be linked to an adjacent substituent to form a ring, for example, an alkyl substituted or unsubstituted indene ring, an alkyl substituted or unsubstituted benzothiophene ring, or an alkyl substituted or unsubstituted benzofuranA ring;
R201to R211Each independently represents hydrogen, deuterium, halogen, deuterium substituted or halogen substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or alkyl substituted or deuterium substituted or unsubstituted (C6-C30) aryl; or may be linked to an adjacent substituent to form a ring, for example, an alkyl substituted or unsubstituted indene ring, an alkyl substituted or unsubstituted benzothiophene ring, or an alkyl substituted or unsubstituted benzofuran ring;
r each independently represents an integer of 1 to 3; when R is 2 or more, R100Each of which may be the same or different; and is
n represents an integer of 1 to 3.
Specific examples of the dopant compound include the following, but are not limited thereto.
The compound represented by formula 1 of the present disclosure may be contained in at least one layer, for example, at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, constituting an organic electroluminescent device. In addition, the compound represented by formula 1 of the present disclosure may be included in the hole transport region, preferably the second hole transport layer of the hole transport region, but is not limited thereto.
The organic electroluminescent material, for example, at least one material of a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transport material, and an electron injection material, may include the compound represented by formula 1 above. The material may be a hole transport region material. The hole transport region material may be composed of only the organic electroluminescent compound represented by formula 1, or may further include conventional materials included in the organic electroluminescent material.
The organic electroluminescent material according to one embodiment may be used as a light emitting material for a white organic light emitting device. According to the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light emitting cells, various structures have been proposed for a white organic light emitting device, such as a parallel side-by-side arrangement method, a stack arrangement method, or a CCM (color conversion material) method, or the like. In addition, the organic electroluminescent material according to one embodiment may also be applied to an organic electroluminescent device including QDs (quantum dots).
An organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. Wherein the first electrode and the second electrode may be each formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be a top emission type, a bottom emission type, or a both-side emission type according to the kind of materials forming the first electrode and the second electrode. The organic layer may include at least one light emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer.
The organic electroluminescent device layer according to the present disclosure may include the organic electroluminescent compound represented by formula 1 above, and may further include conventional materials included in organic electroluminescent materials. The organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 above may exhibit high luminous efficiency and/or long life characteristics.
Further, the present disclosure may provide a display device by using the compound represented by formula 1. That is, a display device or a lighting device can be manufactured using the compound of the present disclosure. Specifically, the organic electroluminescent compounds of the present disclosure may be used to manufacture display devices such as smart phones, tablet computers, notebook computers, PCs, TVs, or vehicle display devices, or lighting devices such as outdoor or indoor lighting.
Hereinafter, the preparation method of the compound according to the present disclosure and the characteristics thereof will be described in detail with reference to representative compounds of the present disclosure in order to understand the present disclosure in detail. However, the present disclosure is not limited to the following examples.
[ example 1] preparation of Compound C-123
1) Preparation of Compound 1-1
Compound A (37g, 205.05mmol), 2-bromo-6-chlorobenzaldehyde (30g, 136.7mmol), tetrakis (triphenylphosphine) palladium (4.7g, 4.1mmol), potassium carbonate (47.2g, 341.75mmol), 400mL tetrahydrofuran, and 100mL distilled water were added to a reaction vessel and stirred at 100 ℃ for 4 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed therefrom with a rotary evaporator. Thereafter, the remaining product was purified by column chromatography to obtain compound 1-1(35g, yield: 94%).
2) Preparation of Compounds 1-2
Compound 1-1(35g, 128.32mmol) and (methoxymethyl) triphenylphosphonium chloride (66g, 192.48mmol) were added to 350mL of tetrahydrofuran in a reaction vessel; thereafter, 193mL of potassium tert-butoxide (1M) were added dropwise to the mixture at 0 ℃. After completion of the dropwise addition, the reaction temperature was slowly raised to room temperature, and the mixture was further stirred for 2 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the extracted organic layer was dried with magnesium sulfate. Thereafter, the solvent was removed therefrom with a rotary evaporator, and then the remaining product was purified by column chromatography to obtain compound 1-2(31g, yield: 80%).
3) Preparation of Compounds 1-3
After dissolving Compound 1-2(31g, 103.06mmol) in chlorobenzene, 3.1mL of Eton's reagent was slowly added dropwise to the reaction vessel. After completion of the dropwise addition, the mixture was further stirred for 2 hours. After completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed therefrom with a rotary evaporator. Thereafter, the remaining product was purified by column chromatography to obtain compounds 1-3(24.4g, yield: 88%).
4) Preparation of Compound C-123
Compound 1-3(3.5g, 13.02mmol), N, 9-diphenyl-9H-carbazol-2-amine (4.8g, 14.33mmol), tris (dibenzylideneacetone) dipalladium (0) (0.6g, 0.65mmol), tri-tert-butylphosphine (0.3mL, 1.30mmol), sodium tert-butoxide (1.9g, 19.53mmol), and 65mL of toluene were added to the reaction vessel and refluxed for 1 hour. Cooling the reaction mixture to room temperature; thereafter, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound C-123(6g, yield: 81%).
| MW | Melting Point | |
| C-123 | 566.71 | 255℃ |
[ example 2] preparation of Compound C-124
The compounds 1-3(3.0g, 11.16mmol), N ([1, 1' -biphenyl ] -2-yl) -9-phenyl-9H-carbazol-2-amine (5.0g, 12.28mmol), tris (dibenzylideneacetone) dipalladium (0) (0.5g, 0.56mmol), tri-tert-butylphosphine (0.3mL, 1.12mmol), sodium tert-butoxide (1.6g, 16.74mmol), and 56mL of toluene were added to the reaction vessel and refluxed for 1 hour. Cooling the reaction mixture to room temperature; thereafter, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound C-124(2g, yield: 28%).
| MW | Melting Point | |
| C-124 | 642.81 | 228℃ |
[ example 3] preparation of Compound C-125
The compound 1-3(3.5g, 13.02mmol), N- ([1, 1' -biphenyl ] -2-yl) -9, 9-dimethyl-9H-fluoren-2-amine (5.2g, 14.33mmol), tris (dibenzylideneacetone) dipalladium (0) (0.6g, 0.65mmol), tri-tert-butylphosphine (0.3mL, 1.30mmol), sodium tert-butoxide (1.9g, 19.53mmol), and 65mL of toluene were added to a reaction vessel and refluxed for 1 hour. Cooling the reaction mixture to room temperature; thereafter, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound C-125(1.3g, yield: 17%).
| MW | Melting Point | |
| C-125 | 593.78 | 250℃ |
Hereinafter, the characteristics of the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure will be explained in order to understand the present disclosure in detail. However, the following example descriptions are intended to explain the features of the OLED according to the present disclosure in order to understand the present disclosure in detail, and the present disclosure is not intended to limit the following examples in any way.
Device examples 1 to 3 production of OLED containing organic electroluminescent Compound according to the present disclosure
An OLED is produced by using the organic electroluminescent compound of the present disclosure. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) (geomama co., LTD., japan) on a glass substrate for an OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, and then stored in isopropyl alcohol. Next, the ITO substrate was mounted on a substrate holder of the vacuum vapor deposition apparatus. Introducing the compound HI-1 into a chamber of a vacuum vapor deposition apparatus, and then controlling the pressure in the chamber of the apparatus to 10-6And (4) supporting. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 90nm on the ITO substrate. Then, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. Next, the compound HT-1 was introduced into another chamber of the vacuum vapor deposition apparatus. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole transporting region having a thickness of 10nm on the second hole injecting layer. Then, the compound of table 1 below (second hole transport material) was introduced into another cell of the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport region (auxiliary layer) having a thickness of 60nm on the first hole transport region. After the hole injection layer and the hole transport region are formed, a light emitting layer is then deposited as follows. The compound H-1 as a host was introduced into one cell of the vacuum vapor deposition apparatus, and the compound D-71 as a dopant was introduced into the other cell of the apparatus. The dopant was deposited in a doping amount of 2 wt% based on the total weight of the host and the dopant to form a light emitting layer having a thickness of 40nm on the hole transporting region. Next, compounds ET-1 and EI-1 were introduced into another cell, evaporated at a rate of 1:1, and deposited to form an electron transport layer having a thickness of 35nm on the light emitting layer. Next, the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, and an electron injection layer having a thickness of 1500 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatusnm thick Al cathode and thereby producing an OLED.
Comparative examples 1 and 2 production of OLED Using Compounds not according to the present disclosure
OLEDs were produced in the same manner as in device examples 1 to 3, except that the compounds of table 1 below were used in the second hole transport region.
The compounds used in the apparatus examples 1 to 3 and comparative examples 1 and 2 are shown below.
The results of the driving voltage, power efficiency, and CIE color coordinates of the OLED produced as described above at 1,000 nits luminance are shown in table 1 below.
TABLE 1
In addition, the time taken for the device example 2 and the comparative example 1 to decrease to 98% at a constant current based on 5,000 nit brightness (lifetime; T98) was 98 hours and 18 hours, respectively.
In the above device examples and comparative examples, it was confirmed that the organic electroluminescent device including the organic electroluminescent compound of the present disclosure had a low driving voltage and/or high power efficiency, as compared to the organic electroluminescent device not including the compound of the present disclosure. Simultaneously or alternatively, the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure may have improved life characteristics.
Claims (8)
1. An organic electroluminescent compound represented by the following formula 1:
wherein the content of the first and second substances,
x represents O or S;
Ar1to Ar4Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or Ar1And Ar2And Ar3And Ar4May be linked to each other to form a ring;
L1and L2Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
R1and R2Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;
a represents an integer of 1 to 4, b represents an integer of 1 to 5, and when a and b are 2 or more, R1Each of (1) and R2Each of which may be the same or different; and is
p and q each independently represent 0 or 1, provided that the sum of p and q is 1 or 2, and when the sum of p and q is 2, L1And L2And Ar1To Ar4May be the same or different.
2. The organic electroluminescent compound according to claim 1, wherein, substituted (C1-C30) alkyl, substituted (C6-C30) (arylene), substituted (3-to 30-membered) (arylene) heteroaryl, substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted tri (C1-C30) alkylsilyl, substituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted tri (C6-C30) arylsilyl, substituted mono-or di- (C1-C30) alkylamino, substituted mono-or di- (C6-C30) arylamino, and substituted (C1-C30) alkyl (C6-C30) arylamino each independently represent at least one substituent selected from the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or unsubstituted (3-to 30-membered) heteroaryl, (3-to 30-membered) heteroaryl substituted or unsubstituted (C6-C30) aryl, tri (C1-C7) alkylsilyl, tri (C6-C30) arylsilyl, di (C30-C30) alkyl (C30-C30) arylsilyl, (C30-C36 30 2) arylsilyl, Amino, mono-or di- (C1-C30) alkylamino, (C1-C30) alkyl-substituted or unsubstituted mono-or di- (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylborarbonyl, di (C1-C30) alkylborarbonyl, (C1-C30) alkyl (C6-C30) arylborarbonyl, (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl.
3. The organic electroluminescent compound according to claim 1, wherein the formula 1 is represented by any one of the following formulae 2 to 4:
wherein the content of the first and second substances,
p and q each independently represent 0 or 1, wherein the sum of p and q is 1; and is
X、Ar1To Ar4、L1、L2、R1、R2A, and b are as defined in claim 1.
4. The organic electroluminescent compound according to claim 1, Ar1To Ar4Each independently represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (3-to 25-membered) heteroaryl group, a substituted or unsubstituted mono-or di- (C1-C20) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C25) arylamino group, or a substituted or unsubstituted (C1-C20) alkyl (C6-C25) arylamino group;
L1and L2Each independently represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-to 25-membered) heteroarylene;
R1and R2Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-to 25-membered) heteroaryl; and is
p and q each independently represent 0 or 1, provided that the sum of p and q is 1.
5. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
6. an organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
8. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent compound is contained in a hole transport region.
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| KR1020190078713A KR20200004257A (en) | 2018-07-03 | 2019-07-01 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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| CN112430225B (en) * | 2020-10-30 | 2022-05-17 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, electronic component, and electronic device |
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| KR20170030289A (en) * | 2015-09-09 | 2017-03-17 | 삼성에스디아이 주식회사 | Organic compound and organic optoelectric device and display device |
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| KR102211337B1 (en) * | 2016-05-19 | 2021-02-03 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20180011980A (en) * | 2016-07-26 | 2018-02-05 | 에스에프씨 주식회사 | Novel heterocyclic compounds and organic light-emitting diode including the same |
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| KR20170030289A (en) * | 2015-09-09 | 2017-03-17 | 삼성에스디아이 주식회사 | Organic compound and organic optoelectric device and display device |
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| CN111349063A (en) * | 2018-12-21 | 2020-06-30 | 乐金显示有限公司 | Organic light emitting device |
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