WO2021118086A2 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
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- WO2021118086A2 WO2021118086A2 PCT/KR2020/016143 KR2020016143W WO2021118086A2 WO 2021118086 A2 WO2021118086 A2 WO 2021118086A2 KR 2020016143 W KR2020016143 W KR 2020016143W WO 2021118086 A2 WO2021118086 A2 WO 2021118086A2
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- 150000002894 organic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- 239000011368 organic material Substances 0.000 claims abstract description 27
- 239000010410 layer Substances 0.000 claims description 172
- 239000000463 material Substances 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 125000004429 atom Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- -1 alkyl boron Chemical compound 0.000 claims description 16
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 16
- 125000005104 aryl silyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 16
- 125000005264 aryl amine group Chemical group 0.000 claims description 14
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- 238000000034 method Methods 0.000 claims description 13
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 8
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
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- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
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- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims description 4
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XRMZKCQCINEBEI-UHFFFAOYSA-N 4-bromo-2-fluoro-1-iodobenzene Chemical compound FC1=CC(Br)=CC=C1I XRMZKCQCINEBEI-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
- UGMQPXUYVGQCSR-UHFFFAOYSA-N Brc(cc1)cc(S2)c1-c1cccc3c1c2ccc3 Chemical compound Brc(cc1)cc(S2)c1-c1cccc3c1c2ccc3 UGMQPXUYVGQCSR-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- XEXVFYMFQPTRRO-UHFFFAOYSA-N C1=CC2=C(C(=C1)S)C(=CC=C2)I Chemical compound C1=CC2=C(C(=C1)S)C(=CC=C2)I XEXVFYMFQPTRRO-UHFFFAOYSA-N 0.000 description 1
- FXHGBACNYDFALU-UHFFFAOYSA-N CC1(C)OB(c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)OC1(C)C Chemical compound CC1(C)OB(c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)OC1(C)C FXHGBACNYDFALU-UHFFFAOYSA-N 0.000 description 1
- GRKDUGYVFFSICC-UHFFFAOYSA-N COC(=O)C=1C=CC=C2C=CC=C(C=12)B(O)O Chemical compound COC(=O)C=1C=CC=C2C=CC=C(C=12)B(O)O GRKDUGYVFFSICC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 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
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000004653 anthracenylene group Chemical group 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- NOOJXHKESAQCMU-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3ccc(-c4c5c(S6)cccc5ccc4)c6c3)ccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3ccc(-c4c5c(S6)cccc5ccc4)c6c3)ccc2)n1 NOOJXHKESAQCMU-UHFFFAOYSA-N 0.000 description 1
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- 239000006229 carbon black Substances 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 238000003618 dip coating Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 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
- 125000000524 functional group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 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
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002985 plastic film Substances 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl 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
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 238000005406 washing Methods 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
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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- C07D405/10—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 linked by a carbon chain containing aromatic 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
- C07D409/02—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
- C07D409/10—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 carbon chain containing aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to a compound excellent in carrier transport ability, luminescent ability and heat resistance, and luminous efficiency, driving voltage, lifespan, etc. by including the compound in one or more organic material layers It relates to an organic electroluminescent device with improved properties.
- 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, etc. according to their function.
- the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing a better natural color according to the light emitting color.
- a host/dopant system may be used as a light emitting material.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- the hole injection layer, the hole transport layer. NPB, BCP, Alq 3 and the like are widely known as the material for the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as the material for the light emitting layer.
- metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
- the present invention has excellent heat resistance, carrier transport ability, light emitting ability, etc., so that it can be used as an organic layer material of an organic electroluminescent device, specifically, a light emitting layer material, a life improvement layer material, a light emitting auxiliary layer material, and/or an electron transport layer material. It aims to provide novel compounds.
- the present invention provides a compound represented by the following formula (1).
- Z 1 To Z 3 are the same as or different from each other, and each independently C(R 1 ) or N, provided that at least two of Z 1 To Z 3 are N,
- Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl Boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 Monoarylphosphinyl group, C 6 ⁇ C 60 Diarylphosphinyl group, C 6 ⁇
- L is a single bond, or is selected from the group consisting of a C 6 ⁇ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
- A is a substituent represented by any one of Formula 1a or Formula 1b,
- X is a single bond or is selected from the group consisting of O, S and CR 2 R 3 ,
- n is an integer from 0 to 3
- m is an integer from 0 to 6
- R 1 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 of Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphinyl group
- Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 Heteroary
- the present invention provides an electron transport layer or an electron transport auxiliary layer comprising the compound represented by the above formula (1).
- the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is an organic electroluminescence containing a compound represented by Formula 1 provide the element.
- the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer.
- the compound represented by Formula 1 may be included as a phosphorescent host material of the emission layer, and an electron transport material of the electron transport layer and the electron transport auxiliary layer.
- the compound represented by Formula 1 has excellent heat resistance, carrier transport ability, light emitting ability, and the like, and thus can be used as an organic material layer material of an organic electroluminescent device.
- the compound represented by Formula 1 of the present invention when used as a phosphorescent host, electron transport layer or electron transport auxiliary layer material, compared to conventional host materials or electron transport materials, high thermal stability, low driving voltage, fast mobility, and high current efficiency and long life characteristics.
- the organic electroluminescent device containing the compound represented by Formula 1 can greatly improve aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.
- the effect according to the present invention is not limited by the contents exemplified above, and more various effects are included in the present specification.
- a nitrogen-containing heteroaromatic ring eg, azine
- a benzoxanthene (A)-based moiety are positioned at both ends of the molecule, and they are directly connected or a separate linker It has a basic skeletal structure connected through (L).
- the compound of Formula 1 is a nitrogen-containing aromatic ring (eg, pyrazine, pyrimidine, triazine) which is a type of a benzoxanthine-based moiety as an electron donor group (EDG) and an azine group as an electron withdrawing group (EWG) with high electron absorption. ) at the same time.
- EDG electron donor group
- EWG electron withdrawing group
- the electron transfer speed is improved, and thus it is possible to have physicochemical properties more suitable for electron injection and electron transport.
- the compound of Formula 1 When the compound of Formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can accept electrons from the cathode well and thus smoothly transfer electrons to the light emitting layer, thereby lowering the driving voltage of the device and improving high efficiency and long lifespan can induce As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.
- the benzoxanthine-based moiety adopted in the present invention exhibits high luminous efficiency compared to conventional dibenzo-based moieties or anthracene derivatives, and has a structure in which color coordinates can be easily tuned.
- the compound of Formula 1 including such a benzoxanthine-based moiety has a triplet energy as high as 2.3 eV or more.
- an electron withdrawing group (EWG) of azines is introduced into the basic skeleton in which a xanthine derivative having a wide singlet energy level and a high triplet energy level is condensed, so that the energy level is high.
- the compound represented by Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material in addition to the host of the light emitting layer.
- the compound of Formula 1 described above is a bipolar compound, so that hole injection/transport capability, luminous efficiency, driving voltage, lifespan characteristics, durability, and the like can be improved.
- the electron transport ability and the like can be improved depending on the type of the introduced substituent.
- the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a light emitting layer material.
- the compound represented by Formula 1 is not only very advantageous for electron transport, but also shows low driving voltage, high efficiency, and long lifespan characteristics.
- the excellent electron transport ability of these compounds can have high efficiency and fast mobility in the organic electroluminescent device, and it is easy to control the HOMO and LUMO energy levels according to the direction or position of the substituent. Therefore, it is possible to exhibit high electron transport properties in an organic electroluminescent device using such a compound.
- the red and green light emitting layers of the organic EL device use phosphorescent materials, respectively, and their technological maturity is high.
- the blue light emitting layer includes a fluorescent material and a phosphorescent material.
- the fluorescent material is in a state in which performance improvement is required, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, since the blue light emitting layer has a high development possibility and a relatively high technical difficulty, there is a limit in improving the performance (eg, driving voltage, efficiency, lifespan, etc.) of the blue organic light emitting device having the blue light emitting layer.
- the compound of Formula 1 may be applied as a material for an electron transport layer (ETL) or an electron transport auxiliary layer in addition to the light emitting layer (EML).
- ETL electron transport layer
- EML electron transport auxiliary layer
- the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic electroluminescent device having the same are improved. There is an advantage that you can.
- the compound represented by Formula 1 according to the present invention has a basic skeleton structure in which a benzoxanthene-based moiety and a nitrogen-containing heteroaromatic ring (eg, azine) are connected directly or through a linker (L). .
- the nitrogen-containing heteroaromatic ring is a nitrogen-containing heteroaryl group (eg, azine, Z 1 to Z 3 containing heterocyclic ring) containing at least two nitrogen atoms, which is an electron withdrawing group excellent in electron transport (Electron Withdrawing Group, EWG) is a kind of
- Z 1 to Z 3 are the same as or different from each other, and are each independently C(R 1 ) or N, but At least two of Z 1 to Z 3 are N.
- Z 1 to Z 3 include 2 to 3 N.
- These triazines, pyrimidines, pyrazines, etc. are a type of 6-membered heterocyclic ring with high electron withdrawing group (EWG) characteristics including 2 to 3 nitrogens, respectively, and thus exhibit excellent electron absorption characteristics, which is advantageous for electron injection and transport.
- EWG electron withdrawing group
- a plurality of R 1 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 of Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 the arylboronic group, C 6 ⁇ C 60 aryl phosphazene group, C 6 ⁇ C 60 mono-aryl phosphonium blood group, C 6 ⁇ C 60 of the diaryl P
- a plurality of R 1 are the same as or different from each other, and each independently hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a group consisting of a heteroaryl group having 5 to 60 nuclear atoms It is preferably selected from
- Ar 1 and Ar 2 may be substituted as various substituents, respectively.
- Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 of Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 An aryl boron group of, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphiny
- Ar 1 and Ar 2 are each independently a C 1 ⁇ C 40 alkyl group, a C 6 ⁇ C 60 aryl group, a heteroaryl group of 5 to 60 nuclear atoms, a C 6 ⁇ C 60 aryloxy group, It may be selected from a C 6 ⁇ C 60 arylphosphine oxide group and a C 6 ⁇ C 60 arylamine group, preferably in a C 6 ⁇ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms. can be selected.
- Ar 1 and Ar 2 are each independently a C 6 ⁇ C 18 aryl group, but these may be different from each other.
- the nitrogen- containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring) may be more specific to any one selected from the group of substituents represented by the following A-1 to A-3.
- the present invention is not limited thereto.
- R 1 , Ar 1 , and Ar 2 are each as defined in Formula 1;
- a monocyclic heteroaromatic ring is specifically exemplified as a nitrogen-containing heteroaromatic ring (eg, a ring containing Z 1 to Z 3 ).
- a nitrogen-containing heteroaromatic ring eg, a ring containing Z 1 to Z 3
- the present invention is not limited thereto, and the use of conventional polycyclic, condensed, and/or fused nitrogen-containing heteroaromatic rings known in the art is also within the scope of the present invention.
- the aforementioned nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring, azine group) may be directly bonded to a benzoxanthene-based moiety or may be bonded through a separate linker (L).
- a separate linker (L) exists between the azine group and the benzoxanthine-based moiety, the HOMO region is extended to give a benefit to the HOMO-LUMO distribution, and the charge transfer efficiency can be increased through the appropriate overlap of the HOMO-LUMO. have.
- the linker (L) may be a linker of a conventional divalent group known in the art.
- L may be a single bond (eg, a direct bond) or a C 6 ⁇ C 18 arylene group and may be selected from the group consisting of a heteroarylene group having 5 to 18 nuclear atoms.
- L may be a single bond, or an arylene group moiety of the following formula (2).
- n is an integer of 1 to 2.
- the moiety of Formula 2 may be an arylene group linker known in the art, and specific examples thereof include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolyl group. Rene group, thiophenylene group, indolylene group, purinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazolylene group, pyridinylene group, pyrimidinylene group, and the like. More specifically, the linker (L) represented by Formula 2 may be a phenylene group or a biphenylene group.
- the linker of Formula 2 may be a linker selected from the following structural formulas.
- linker (L) is not specifically shown in the formula, at least one or more substituents known in the art (eg, R 1 ) may be substituted.
- the compound represented by Formula 1 of the present invention is a direct bond or linker (L) on one side of a nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring), which is a kind of electron withdrawing group (EWG) having excellent electron transport ability. It is bound to a benzoxanthine-based moiety (eg, A) through The benzoxanthine-based moiety (A) may be any one of Formula 1a or Formula 1b below.
- X may be a single bond or may be selected from the group consisting of O, S and CR 2 R 3 .
- R 2 To R 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphinyl group, C
- R 2 To R 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and the number of nuclear atoms 5 It may be selected from the group consisting of to 60 heteroaryl groups.
- R 4 substituted in the benzoxanthine-based moiety (A) represented by Formula 1a or 1b may be a conventional substituent known in the art, and is not particularly limited. For example, it may be the same as the definition of R 2 to R 3 described above.
- the number (m) of R 4 is not particularly limited, and may be an integer of 0 to 6, for example.
- R 4 when m is 0, R 4 is hydrogen, and when m is 1 to 6, R 4 may have the aforementioned substituents other than hydrogen.
- the benzoxanthine-based moiety (A) may be further specified by the following structural formula.
- benzoxanthine-based moiety (A) embodied in the above-mentioned structural formula is not specifically shown in the formula, at least one or more substituents known in the art (eg, R 4 ) may be substituted.
- L is an arylene group or a heteroarylene group
- Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, nuclear atom
- the compound represented by Chemical Formula 1 may be more specific to the following Chemical Formula 3 or 4 depending on the type of the benzoxanthine-based moiety (A).
- Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Chemical Formula 1.
- the compound represented by Formula 3 may be more specific to any one of the following Formulas 5 to 8 depending on the bonding position of the linker (L) connected to the benzoxanthine-based core.
- the present invention is not limited thereto.
- Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Chemical Formula 1.
- the compound represented by Chemical Formula 4 may be more specific to any one of the following Chemical Formulas 9 to 12 depending on the bonding position of the linker (L) connected to the benzoxanthine-based core.
- the present invention is not limited thereto.
- Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Formula 1.
- Z 1 to Z 3 are N, and Ar 1 and Ar 2 are the same as or different from each other, and each independently C 6 ⁇ C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.
- L is a single bond or a C 6 ⁇ C 18 arylene group, and n is an integer of 1 to 2.
- R 1 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and 5 to 60 nuclear atoms It is selected from the group consisting of a heteroaryl group, and m is an integer from 0 to 6.
- the arylene group of L; Ar 1 and Ar 2 An aryl group, a heteroaryl group; And R 1 To R 4 Alkyl group, aryl group, heteroaryl group is each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, It may be substituted with one or more substituents selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60. In this case, when the substituents are plural, they may be the same or different from each other.
- the compound represented by Formula 1 of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by 1 to 200.
- the compound represented by Formula 1 of the present invention is not limited by those exemplified below.
- alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
- alkenyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like.
- alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined.
- two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms.
- one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazo
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
- R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
- arylamine means an amine substituted with an aryl having 6 to 40 carbon atoms.
- cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se.
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl refers to silyl substituted with aryl having 5 to 40 carbon atoms.
- condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
- the present invention provides an electron transport layer comprising the compound represented by Formula 1 above.
- the electron transport layer serves to move electrons injected from the cathode to an adjacent layer, specifically, the light emitting layer.
- the compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
- ETL electron transport layer
- the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
- the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compound, aluminum complex (eg, Alq 3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complex (eg, Gaq'2OPiv, Gaq) '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.
- the compound of Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited, and may be appropriately adjusted within a range known in the art.
- the present invention provides an electron transport auxiliary layer including the compound represented by the formula (1).
- the electron transport layer is disposed between the emission layer and the electron transport layer, and serves to prevent the excitons or holes generated in the emission layer from diffusing into the electron transport layer.
- the compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
- the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
- the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a nitrogen-containing heterocyclic derivative, and the like.
- the compound of Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and may be appropriately adjusted within a range known in the art.
- organic electroluminescent device including the compound represented by Formula 1 according to the present invention.
- the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above.
- the compound may be used alone or in combination of two or more.
- the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer is represented by Formula 1 compounds.
- the organic material layer including the compound of Formula 1 is a light emitting layer (more specifically, a phosphorescent light emitting host material), an electron transport layer, and an electron transport auxiliary layer.
- the light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and in this case, the compound of Formula 1 may be included as the host material.
- the light emitting layer of the present invention may include a known compound in the art other than the compound of Formula 1 as a host.
- the compound represented by Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic electroluminescent device (luminous efficiency and power efficiency), lifespan, luminance, and driving voltage can be improved.
- the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material.
- the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light emitting layer having high efficiency.
- the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
- at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably the light emitting layer, more preferably a phosphorescent host may include a compound represented by Formula 1 above.
- an electron injection layer may be additionally stacked on the electron transport layer.
- the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
- the organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. have.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
- the substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet may be used.
- a cathode material a cathode material known in the art may be used without limitation.
- metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides 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 or polyaniline; and carbon black, but is not limited thereto.
- a negative electrode material a negative electrode material known in the art may be used without limitation.
- a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.
- the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.
- a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After cleaning with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech) The substrate was transferred to a vacuum evaporator.
- ITO indium tin oxide
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound 6 as the electron transport layer material.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the electron transport layer material was not included.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 was used instead of Compound 6 as the electron transport layer material.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-2 was used instead of Compound 6 as the electron transport layer material.
- the blue organic electroluminescent devices of Examples 1 to 8 using the compound of the present invention as an electron transport layer material the blue organic electroluminescent device of Comparative Example 1 using Alq 3 as an electron transport layer material in the prior art ; And it was found that the blue organic EL device of Comparative Example 2 not including an electron transport layer exhibits significantly superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic EL device of Comparative Example 2.
- a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is performed and dried, transferred to a UV OZONE washer (Power sonic 405, Hwashin Tech), and then the substrate is washed using UV for 5 minutes and transferred the substrate to a vacuum evaporator.
- ITO indium tin oxide
- a blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound 56 was not used as an electron transport auxiliary layer material, and Alq 3, an electron transport layer material, was deposited at 30 nm instead of 25 nm. .
- a blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound A-1 was used instead of Compound 56 as an electron transport auxiliary layer material.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound A-2 was used instead of Compound 56 as an electron transport auxiliary layer material.
- Example 9 compound 56 3.1 454 8.0
- Example 10 compound 63 3.0 454 8.1
- Example 11 compound 66 3.2 454 8.2
- Example 12 compound 68 3.1 454 8.1
- Example 13 compound 181 3.1 454 8.0
- Example 14 compound 188 3.2 454 8.1
- Example 15 compound 191 3.1 455 8.2
- Example 16 compound 193 3.2 454 8.3 Comparative Example 5 - 4.7 459 6.1 Comparative Example 6 A-1 4.3 459 5.9 Comparative Example 7 A-2 4.8 455 5.3
- the blue organic electroluminescent devices of Examples 9 to 16 using the compound of the present invention as an electron transport auxiliary layer material were the blue organic electroluminescent devices of Comparative Example 5 without an electron transport auxiliary layer. Compared to that, it showed excellent performance in terms of current efficiency and luminescence peak, and particularly in terms of driving voltage.
- the blue organic electroluminescent devices of 9 to 16 are of Comparative Example 6 including an electron transport auxiliary layer material having a conventional dibenzo-based moiety and a fluorene group, and Comparative Example 7 including an electron transport layer material not including an azine group It was found that the blue organic EL device exhibited superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic EL device.
Abstract
The present invention relates to: a novel compound having excellent carrier transport capability, luminescence capability, and thermal stability; and an organic electroluminescent device which, by comprising same in at least one organic material layer, has improved characteristics such as improved luminous efficiency, driving voltage, and lifespan.
Description
본 발명은 신규한 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 캐리어 수송능, 발광능 및 내열성이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to a compound excellent in carrier transport ability, luminescent ability and heat resistance, and luminous efficiency, driving voltage, lifespan, etc. by including the compound in one or more organic material layers It relates to an organic electroluminescent device with improved properties.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Beginning with the observation of organic thin film emission by Bernanose in the 1950s, research on organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals continued in 1965. ) presented an organic electroluminescent device having a stacked structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of a specialized material used for this.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 물질 등으로 분류될 수 있다.In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. In this case, 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, etc. according to their function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing a better natural color according to the light emitting color. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as the phosphorescent dopant is in progress.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq
3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)
3, (acac)Ir(btp)
2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.To date, the hole injection layer, the hole transport layer. NPB, BCP, Alq 3 and the like are widely known as the material for the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as the material for the light emitting layer. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, conventional organic material layer materials are advantageous in terms of luminescent properties, but have not been satisfactory in terms of the lifespan of the organic electroluminescent device because the thermal stability is not very good due to the low glass transition temperature. Accordingly, there is a demand for the development of an organic layer material having excellent performance.
본 발명은 내열성, 캐리어 수송능, 발광능 등이 우수하여 유기 전계 발광 소자의 유기물 층 재료, 구체적으로 발광층 재료, 수명 개선층 재료, 발광 보조층 재료, 및/또는 전자 수송층 재료 등으로 사용될 수 있는 신규 화합물을 제공하는 것을 목적으로 한다.The present invention has excellent heat resistance, carrier transport ability, light emitting ability, etc., so that it can be used as an organic layer material of an organic electroluminescent device, specifically, a light emitting layer material, a life improvement layer material, a light emitting auxiliary layer material, and/or an electron transport layer material. It aims to provide novel compounds.
또한, 본 발명은 전술한 신규 화합물을 포함하여 구동전압이 낮고, 발광 효율이 높으며, 수명이 향상된 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, it is another object of the present invention to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound described above.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1).
Z
1 내지 Z
3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C(R
1) 또는 N이고, 다만 Z
1 내지 Z
3 중 적어도 2개는 N이며, Z 1 To Z 3 Are the same as or different from each other, and each independently C(R 1 ) or N, provided that at least two of Z 1 To Z 3 are N,
Ar
1 및 Ar
2는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
3~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스파닐기, C
6~C
60의 모노아릴포스피닐기, C
6~C
60의 디아릴포스피닐기, C
6~C
60의 아릴아민기, C
5~C
60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택되며, Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl Boron group, C 6 ~ C 60 Arylphosphanyl group, C 6 ~ C 60 Monoarylphosphinyl group, C 6 ~ C 60 Diarylphosphinyl group, C 6 ~ C 60 Arylamine group, C 5 ~ C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms,
L은 단일결합이거나, 또는 C
6~C
18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고, L is a single bond, or is selected from the group consisting of a C 6 ~ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
A는 하기 화학식 1a 또는 화학식 1b 중 어느 하나로 표시되는 치환기이며,A is a substituent represented by any one of Formula 1a or Formula 1b,
[화학식 1a][Formula 1a]
[화학식 1b][Formula 1b]
상기 화학식 1a 또는 1b에서, In Formula 1a or 1b,
*는 상기 화학식 1에 결합되는 부분을 의미하고, * means a moiety bonded to Formula 1,
X는 단일결합이거나 또는 O, S 및 CR
2R
3로 이루어진 군에서 선택되며,X is a single bond or is selected from the group consisting of O, S and CR 2 R 3 ,
n은 0 내지 3의 정수이며, m은 0 내지 6의 정수이며,n is an integer from 0 to 3, m is an integer from 0 to 6,
R
1 내지 R
4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
3~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스파닐기, C
6~C
60의 모노아릴포스피닐기, C
6~C
60의 디아릴포스피닐기, C
6~C
60의 아릴아민기, C
5~C
60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택되며;R 1 To R 4 Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 of Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Monoaryl phosphinyl group, C 6 ~ C 60 Diaryl phosphinyl group, C 6 ~ C 60 Arylamine group, C 5 ~ C 60 It is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms;
상기 L의 아릴렌기, 헤테로아릴렌기와; Ar
1 내지 Ar
2, 및 R
1 내지 R
4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
1~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스핀기, C
6~C
60의 아릴포스핀옥사이드기, C
6~C
60의 아릴아민기, C
5~C
60의 아릴헤테로아릴아민기, 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. an arylene group and a heteroarylene group of L; Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 Heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 groups of an alkyl boron, C 6 ~ aryl boronic of C 60, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, C 6 ~ C 60 aryl amine group, C 5 ~ C 60 may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when the substituents are plural, they may be the same or different from each other can
또한 본 발명은 전술한 화학식 1로 표시되는 화합물을 포함하는 전자수송층 또는 전자수송 보조층을 제공한다. In addition, the present invention provides an electron transport layer or an electron transport auxiliary layer comprising the compound represented by the above formula (1).
아울러, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하고, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다. In addition, the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is an organic electroluminescence containing a compound represented by Formula 1 provide the element.
여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층, 전자수송 보조층 및 전자 주입층으로 이루어진 군에서 선택될 수 있다. 이때 화학식 1로 표시되는 화합물은 발광층의 인광 호스트 재료, 전자 수송층 및 전자수송 보조층의 전자 수송 재료로 포함될 수 있다.Here, the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer. In this case, the compound represented by Formula 1 may be included as a phosphorescent host material of the emission layer, and an electron transport material of the electron transport layer and the electron transport auxiliary layer.
본 발명의 일 실시예에 따르면, 상기 화학식 1로 표시되는 화합물은 내열성, 캐리어 수송능, 발광능 등이 우수하기 때문에, 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있다.According to an embodiment of the present invention, the compound represented by Formula 1 has excellent heat resistance, carrier transport ability, light emitting ability, and the like, and thus can be used as an organic material layer material of an organic electroluminescent device.
특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트, 전자수송층 또는 전자수송 보조층 재료로 사용할 경우 종래의 호스트 재료 또는 전자 수송 재료에 비해 높은 열적 안정성, 낮은 구동전압, 빠른 모빌리티, 높은 전류효율 및 장수명 특성을 나타낼 수 있다. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host, electron transport layer or electron transport auxiliary layer material, compared to conventional host materials or electron transport materials, high thermal stability, low driving voltage, fast mobility, and high current efficiency and long life characteristics.
이에 따라, 상기 화학식 1로 화합물을 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상될 수 있고, 따라서 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.Accordingly, the organic electroluminescent device containing the compound represented by Formula 1 can greatly improve aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.
본 발명에 따른 효과는 이상에서 예시된 내용에 의해 제한되지 않으며, 보다 다양한 효과들이 본 명세서 내에 포함되어 있다.The effect according to the present invention is not limited by the contents exemplified above, and more various effects are included in the present specification.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
<유기 화합물><Organic compound>
본 발명에 따라 화학식 1로 표시되는 화합물은, 분자의 양 말단에 각각 함질소 헤테로방향족환(예, azine)과 벤조잔틴(benzoxanthene, A)계 모이어티가 위치하고, 이들이 직접 연결되거나 또는 별도의 링커(L)를 통해 연결되는 기본 골격구조를 갖는다. In the compound represented by Formula 1 according to the present invention, a nitrogen-containing heteroaromatic ring (eg, azine) and a benzoxanthene (A)-based moiety are positioned at both ends of the molecule, and they are directly connected or a separate linker It has a basic skeletal structure connected through (L).
구체적으로, 상기 화학식 1의 화합물은 전자주게기(EDG)인 벤조잔틴계 모이어티와 전자흡수성이 큰 전자끌게기(EWG)인 아진기의 일종인 함질소 방향족환(예, pyrazine, pyrimidine, triazine)을 동시에 포함한다. 이와 같이 강한 전자끌개능력(EWG)을 가진 작용기인 아진기를 도입함으로써 전자이동속도를 향상시켜 전자주입 및 전자수송에 더욱 적합한 물리화학적 성질을 가질 수 있게 된다. 전술한 화학식 1의 화합물을 전자수송층 또는 전자수송 보조층의 재료로 적용시, 음극으로부터 전자를 잘 수용할 수 있어 발광층으로 전자를 원활히 전달할 수 있으며, 이에 따라 소자의 구동전압을 낮추고 고효율 및 장수명을 유도할 수 있다. 이러한 유기 전계 발광 소자는 결과적으로 풀 칼라 유기 발광 패널의 성능을 극대화시킬 수 있다.Specifically, the compound of Formula 1 is a nitrogen-containing aromatic ring (eg, pyrazine, pyrimidine, triazine) which is a type of a benzoxanthine-based moiety as an electron donor group (EDG) and an azine group as an electron withdrawing group (EWG) with high electron absorption. ) at the same time. By introducing an azine group, which is a functional group having a strong electron withdrawing capability (EWG) as described above, the electron transfer speed is improved, and thus it is possible to have physicochemical properties more suitable for electron injection and electron transport. When the compound of Formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can accept electrons from the cathode well and thus smoothly transfer electrons to the light emitting layer, thereby lowering the driving voltage of the device and improving high efficiency and long lifespan can induce As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.
특히 본 발명에서 채택한 벤조잔틴계 모이어티는, 종래의 디벤조계 모이어티나 안트라센류 유도체에 비해 높은 발광효율을 보이며, 색좌표의 튜닝이 용이한 구조이다. 이러한 벤조잔틴계 모이어티를 포함하는 상기 화학식 1의 화합물은 삼중항 에너지가 2.3 eV 이상으로 높다. 또한, 상기 화학식 1로 표시되는 화합물은 넓은 일중항 에너지 준위와 높은 삼중항 에너지 준위를 가지는 잔틴 유도체가 축합되어 있는 기본 골격에, 아진류의 전자끄는기(EWG)가 도입되어 에너지 준위가 높게 조절될 수 있기 때문에, 발광층에서 생성된 엑시톤이 발광층에 인접하는 호스트 또는 정공수송층으로 확산되는 것을 방지할 수 있다. 따라서, 상기 화학식 1의 화합물을 이용하여 정공 수송층과 발광층 사이에 유기물층(이하, '발광 보조층'이라 함)을 형성할 경우, 상기 화합물에 의해서 엑시톤의 확산이 방지되기 때문에, 상기 제1 엑시톤 확산 방지층을 포함하지 않은 종래 유기 전계 발광 소자와 달리, 실질적으로 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있다. In particular, the benzoxanthine-based moiety adopted in the present invention exhibits high luminous efficiency compared to conventional dibenzo-based moieties or anthracene derivatives, and has a structure in which color coordinates can be easily tuned. The compound of Formula 1 including such a benzoxanthine-based moiety has a triplet energy as high as 2.3 eV or more. In addition, in the compound represented by Formula 1, an electron withdrawing group (EWG) of azines is introduced into the basic skeleton in which a xanthine derivative having a wide singlet energy level and a high triplet energy level is condensed, so that the energy level is high. Since it is possible, it is possible to prevent the excitons generated in the light emitting layer from diffusing to the host or hole transport layer adjacent to the light emitting layer. Therefore, when an organic material layer (hereinafter, referred to as 'emission auxiliary layer') is formed between the hole transport layer and the light emitting layer using the compound of Formula 1, the diffusion of excitons is prevented by the compound, so that the first exciton diffusion Unlike the conventional organic electroluminescent device that does not include a blocking layer, the number of excitons contributing to light emission in the light emitting layer is substantially increased, so that the luminous efficiency of the device can be improved.
아울러, 상기 화학식 1의 화합물을 이용하여 발광층과 전자 수송층 사이에 유기물층(이하, '수명 개선층'이라 함)을 형성할 경우에도, 상기 화학식 1의 화합물에 의해 엑시톤의 확산이 방지됨으로써, 유기 전계 발광 소자의 내구성 및 안정성이 향상될 수 있고, 이로 인해 소자의 반감 수명이 효율적으로 증가될 수 있다. 이와 같이, 상기 화학식 1로 표시되는 화합물은 발광층의 호스트 이외에, 발광 보조층 재료 또는 수명 개선층 재료로 사용될 수 있다.In addition, even when an organic material layer (hereinafter, referred to as a 'lifetime improvement layer') is formed between the light emitting layer and the electron transport layer using the compound of Formula 1, diffusion of excitons is prevented by the compound of Formula 1, so that the organic electric field Durability and stability of the light emitting device may be improved, and thus the half-life of the device may be effectively increased. As such, the compound represented by Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material in addition to the host of the light emitting layer.
전술한 상기 화학식 1의 화합물은 양극성(bipolar) 화합물이기 때문에, 정공과 전자의 재결합이 높아 정공 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성, 내구성 등을 향상시킬 수 있다. 또한 도입되는 치환체의 종류에 따라 전자 수송 능력 등도 향상시킬 수 있다. 따라서, 상기 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 전자수송층, 전자수송 보조층 재료 및 발광층 재료로 사용될 수 있다.Since the compound of Formula 1 described above is a bipolar compound, the recombination of holes and electrons is high, so that hole injection/transport capability, luminous efficiency, driving voltage, lifespan characteristics, durability, and the like can be improved. In addition, the electron transport ability and the like can be improved depending on the type of the introduced substituent. Accordingly, the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a light emitting layer material.
나아가, 상기 화학식 1로 표시되는 화합물은 전자 수송에 매우 유리할 뿐만 아니라 낮은 구동전압, 높은 효율 및 장수명 특성을 보여준다. 이러한 화합물의 우수한 전자수송 능력은 유기 전계 발광 소자에서 높은 효율과 빠른 이동성(mobility)을 가질 수 있고, 치환기의 방향이나 위치에 따라 HOMO 및 LUMO 에너지 레벨을 조절이 용이하다. 그러므로, 이러한 화합물을 사용한 유기 전계 발광 소자에서 높은 전자 수송성을 나타낼 수 있다.Furthermore, the compound represented by Formula 1 is not only very advantageous for electron transport, but also shows low driving voltage, high efficiency, and long lifespan characteristics. The excellent electron transport ability of these compounds can have high efficiency and fast mobility in the organic electroluminescent device, and it is easy to control the HOMO and LUMO energy levels according to the direction or position of the substituent. Therefore, it is possible to exhibit high electron transport properties in an organic electroluminescent device using such a compound.
한편 유기 전계 발광 소자의 적색 및 녹색 발광층은 각각 인광 재료를 이용하고 있으며, 현재 이들의 기술 성숙도는 높은 상태이다. 이에 비해, 청색 발광층은 형광 재료와 인광 재료가 있는데, 이중 형광 재료는 성능 향상이 필요한 상태이며, 청색 인광재료는 아직 개발 중이어서 진입 장벽이 높은 상태이다. 즉, 청색 발광층은 개발 가능성이 큰 반면 기술난이도가 상대적으로 높기 때문에, 이를 구비하는 청색 유기발광소자의 성능(예, 구동전압, 효율, 수명 등)을 향상시키는데 한계가 있다. 이에, 본 발명에서는 상기 화학식 1의 화합물을 발광층(EML) 이외에, 전자수송층(ETL) 또는 전자수송 보조층 재료로 적용할 수 있다. 이와 같이, 유기 전계 발광 소자에서 공통층(common layer)으로 사용되는 전자수송층 또는 전자수송 보조층의 재료 변화를 통해 발광층, 구체적으로 청색 발광층의 성능과 이를 구비하는 유기 전계 발광 소자의 성능을 향상시킬 수 있다는 이점이 있다.On the other hand, the red and green light emitting layers of the organic EL device use phosphorescent materials, respectively, and their technological maturity is high. In contrast, the blue light emitting layer includes a fluorescent material and a phosphorescent material. Among them, the fluorescent material is in a state in which performance improvement is required, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, since the blue light emitting layer has a high development possibility and a relatively high technical difficulty, there is a limit in improving the performance (eg, driving voltage, efficiency, lifespan, etc.) of the blue organic light emitting device having the blue light emitting layer. Accordingly, in the present invention, the compound of Formula 1 may be applied as a material for an electron transport layer (ETL) or an electron transport auxiliary layer in addition to the light emitting layer (EML). As such, through the material change of the electron transport layer or electron transport auxiliary layer used as a common layer in the organic electroluminescent device, the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic electroluminescent device having the same are improved. There is an advantage that you can.
구체적으로, 본 발명에 따라 화학식 1로 표시되는 화합물은, 벤조잔틴(benzoxanthene)계 모이어티와 함질소 헤테로방향족환(예, azine)이 직접 또는 링커(L)를 통해 연결되는 기본 골격구조를 갖는다.Specifically, the compound represented by Formula 1 according to the present invention has a basic skeleton structure in which a benzoxanthene-based moiety and a nitrogen-containing heteroaromatic ring (eg, azine) are connected directly or through a linker (L). .
상기 함질소 헤테로방향족환은 적어도 2개의 질소 원자를 포함하는 함질소 헤테로아릴기(예, azine, Z
1~Z
3 함유 헤테로환)로서, 이는 전자 수송능이 뛰어난 전자끄는기(Electron Withdrawing Group, EWG)의 일종이다. The nitrogen-containing heteroaromatic ring is a nitrogen-containing heteroaryl group (eg, azine, Z 1 to Z 3 containing heterocyclic ring) containing at least two nitrogen atoms, which is an electron withdrawing group excellent in electron transport (Electron Withdrawing Group, EWG) is a kind of
이러한 함질소 헤테로방향족환(예, Z
1~Z
3 함유 환)의 일 실시예를 들면, Z
1 내지 Z
3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C(R
1) 또는 N이고, 다만 Z
1 내지 Z
3 중 적어도 2개는 N이다. 바람직한 일례를 들면, Z
1 내지 Z
3는 2 내지 3개의 N을 포함한다. 이러한 트리아진, 피리미딘, 피라진 등은 각각 2~3개의 질소를 포함하여 전자끌게기 (EWG) 특성이 높은 6원 헤테로환의 일종이므로, 우수한 전자 흡수특성을 나타내어 전자 주입 및 수송에 유리하다.For an embodiment of such a nitrogen- containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring), Z 1 to Z 3 are the same as or different from each other, and are each independently C(R 1 ) or N, but At least two of Z 1 to Z 3 are N. In a preferred example, Z 1 to Z 3 include 2 to 3 N. These triazines, pyrimidines, pyrazines, etc. are a type of 6-membered heterocyclic ring with high electron withdrawing group (EWG) characteristics including 2 to 3 nitrogens, respectively, and thus exhibit excellent electron absorption characteristics, which is advantageous for electron injection and transport.
여기서, 복수의 R
1은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
3~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스파닐기, C
6~C
60의 모노아릴포스피닐기, C
6~C
60의 디아릴포스피닐기 및 C
6~C
60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 이들은 인접한 기(다른 R
1)와 결합하여 축합 고리를 형성할 수 있다. 구체적으로, 복수의 R
1는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, C
1~C
40의 알킬기, C
6~C
60의 아릴기, 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택되는 것이 바람직하다. Here, a plurality of R 1 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 of Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 the arylboronic group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono-aryl phosphonium blood group, C 6 ~ C 60 of the diaryl Phosphinicosuccinic consisting of groups and C 6 ~ C 60 aryl amine of the group of selected from the group, or they may combine with adjacent groups (other R 1 ) to form a condensed ring. Specifically, a plurality of R 1 are the same as or different from each other, and each independently hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a group consisting of a heteroaryl group having 5 to 60 nuclear atoms It is preferably selected from
상기 함질소 헤테로방향족환(예, Z
1~Z
3 함유 환)에는 다양한 치환체로서 Ar
1 및 Ar
2가 각각 치환될 수 있다. In the nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring), Ar 1 and Ar 2 may be substituted as various substituents, respectively.
이러한 Ar
1 및 Ar
2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
3~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스파닐기, C
6~C
60의 모노아릴포스피닐기, C
6~C
60의 디아릴포스피닐기, C
6~C
60의 아릴아민기, C
5~C
60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택될 수 있다. 구체적으로, Ar
1 및 Ar
2는 각각 독립적으로 C
1~C
40의 알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C
6~C
60의 아릴옥시기, C
6~C
60의 아릴포스핀옥사이드기 및 C
6~C
60의 아릴아민기에서 선택될 수 있으며, 바람직하게는 C
6~C
60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기에서 선택될 수 있다. 보다 바람직한 일례를 들면, Ar
1 및 Ar
2는 각각 독립적으로 C
6~C
18의 아릴기이되, 이들은 서로 상이한 것일 수 있다. These Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 of Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 An aryl boron group of, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Monoaryl phosphinyl group, C 6 ~ C 60 Diaryl phosphinyl group, C 6 ~ C 60 Arylamine group, C 5 ~ C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms. Specifically, Ar 1 and Ar 2 are each independently a C 1 ~ C 40 alkyl group, a C 6 ~ C 60 aryl group, a heteroaryl group of 5 to 60 nuclear atoms, a C 6 ~ C 60 aryloxy group, It may be selected from a C 6 ~ C 60 arylphosphine oxide group and a C 6 ~ C 60 arylamine group, preferably in a C 6 ~ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms. can be selected. For a more preferred example, Ar 1 and Ar 2 are each independently a C 6 ~ C 18 aryl group, but these may be different from each other.
본 발명의 일 구체예를 들면, 함질소 헤테로방향족환(예, Z
1~Z
3 함유 환)은 하기 A-1 내지 A-3로 표시되는 치환체 군에서 선택되는 어느 하나로 보다 구체화될 수 있다. 그러나, 이에 한정되는 것은 아니다. For one embodiment of the present invention, the nitrogen- containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring) may be more specific to any one selected from the group of substituents represented by the following A-1 to A-3. However, the present invention is not limited thereto.
상기 A-1 내지 A-3에서, In A-1 to A-3 above,
*는 상기 화학식 1과 결합이 이루어지는 부분을 의미하며, * means a portion in which a bond is formed with Chemical Formula 1,
R
1, Ar
1 및 Ar
2는 각각 화학식 1에서 정의된 바와 같다. R 1 , Ar 1 , and Ar 2 are each as defined in Formula 1;
한편 본 발명에서는 함질소 헤테로방향족환(예, Z
1~Z
3 함유 환)으로서 단환식 헤테로방향족환을 구체적으로 예시하였다. 그러나 이에 한정되지 않으며, 당 분야에 공지된 통상의 다환식, 축합식, 및/또는 융합 형태의 함질소 헤테로방향족환을 사용하는 것도 본 발명의 범주에 속한다. Meanwhile, in the present invention, a monocyclic heteroaromatic ring is specifically exemplified as a nitrogen-containing heteroaromatic ring (eg, a ring containing Z 1 to Z 3 ). However, the present invention is not limited thereto, and the use of conventional polycyclic, condensed, and/or fused nitrogen-containing heteroaromatic rings known in the art is also within the scope of the present invention.
전술한 함질소 헤테로방향족환(예, Z
1~Z
3 함유 환, 아진기)은 벤조잔틴 (benzoxanthene)계 모이어티에 직접 결합되거나 또는 별도의 링커(L)를 통해 결합될 수 있다. 이와 같이, 아진기와 벤조잔틴계 모이어티 사이에 별도의 링커(L)가 존재할 경우, HOMO 영역을 확장시켜 HOMO-LUMO 분포에 이득을 주고, HOMO-LUMO의 적절한 중첩을 통하여 전하 이동 효율을 높일 수 있다. The aforementioned nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring, azine group) may be directly bonded to a benzoxanthene-based moiety or may be bonded through a separate linker (L). As such, when a separate linker (L) exists between the azine group and the benzoxanthine-based moiety, the HOMO region is extended to give a benefit to the HOMO-LUMO distribution, and the charge transfer efficiency can be increased through the appropriate overlap of the HOMO-LUMO. have.
이러한 링커(L)는 당 분야에 알려진 통상적인 2가(divalent) 그룹의 연결기(Linker)일 수 있다. 일례로, L은 단일결합(예, 직접결합)이거나 또는 C
6~C
18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 구성된 군에서 선택될 수 있다. 일 구체예를 들면, L은 단일결합이거나, 또는 하기 화학식 2의 아릴렌기 모이어티일 수 있다. The linker (L) may be a linker of a conventional divalent group known in the art. For example, L may be a single bond (eg, a direct bond) or a C 6 ~ C 18 arylene group and may be selected from the group consisting of a heteroarylene group having 5 to 18 nuclear atoms. In one embodiment, L may be a single bond, or an arylene group moiety of the following formula (2).
상기 화학식 2에서,In Formula 2,
*는 상기 화학식 1과 결합이 이루어지는 부분을 의미하며, * means a portion in which a bond is formed with Chemical Formula 1,
n은 1 내지 2의 정수이다. n is an integer of 1 to 2.
상기 화학식 2의 모이어티는 당 분야에 공지된 아릴렌기 링커일 수 있으며, 이의 구체적인 예로는 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 피리디닐렌기, 피리미디닐렌기 등이 있다. 보다 구체적으로, 화학식 2로 표시되는 링커(L)는 페닐렌기 또는 비페닐렌기일 수 있다. The moiety of Formula 2 may be an arylene group linker known in the art, and specific examples thereof include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolyl group. Rene group, thiophenylene group, indolylene group, purinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazolylene group, pyridinylene group, pyrimidinylene group, and the like. More specifically, the linker (L) represented by Formula 2 may be a phenylene group or a biphenylene group.
본 발명의 일 구체예를 들면, 화학식 2의 링커는 하기 구조식 중에서 선택되는 연결기(linker)일 수 있다. In one embodiment of the present invention, the linker of Formula 2 may be a linker selected from the following structural formulas.
상기 식에서,In the above formula,
*는 상기 화학식 1과 결합이 이루어지는 부분을 의미한다. * denotes a portion where a bond with Chemical Formula 1 is formed.
전술한 링커(L)는 화학식 상에 구체적으로 표시되지 않았으나, 당 분야에 공지된 치환기(예컨대, R
1)가 적어도 하나 이상 치환될 수 있다. Although the above-mentioned linker (L) is not specifically shown in the formula, at least one or more substituents known in the art (eg, R 1 ) may be substituted.
본 발명의 화학식 1로 표시되는 화합물은, 전자 수송능이 뛰어난 전자끄는기(EWG)의 일종인 함질소 헤테로 방향족환(예, Z
1~Z
3 함유 환)의 일측에 직접결합 또는 링커(L)를 통해 벤조잔틴계 모이어티(예, A)와 결합된다. 이러한 벤조잔틴계 모이어티(A)는 하기 화학식 1a 또는 화학식 1b 중 어느 하나일 수 있다. The compound represented by Formula 1 of the present invention is a direct bond or linker (L) on one side of a nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring), which is a kind of electron withdrawing group (EWG) having excellent electron transport ability. It is bound to a benzoxanthine-based moiety (eg, A) through The benzoxanthine-based moiety (A) may be any one of Formula 1a or Formula 1b below.
[화학식 1a][Formula 1a]
[화학식 1b][Formula 1b]
상기 화학식 1a 또는 1b에서, X는 단일결합이거나 또는 O, S 및 CR
2R
3로 이루어진 군에서 선택될 수 있다. In Formula 1a or 1b, X may be a single bond or may be selected from the group consisting of O, S and CR 2 R 3 .
여기서, R
2 내지 R
3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
3~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스파닐기, C
6~C
60의 모노아릴포스피닐기, C
6~C
60의 디아릴포스피닐기, C
6~C
60의 아릴아민기, C
5~C
60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택될 수 있다. 구체적으로, R
2 내지 R
3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C
1~C
40의 알킬기, C
6~C
60의 아릴기, 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택될 수 있다. Here, R 2 To R 3 Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Monoaryl phosphinyl group, C 6 ~ C 60 Diaryl phosphinyl group, C 6 ~ C 60 Arylamine group , C 5 ~ C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms. Specifically, R 2 To R 3 Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, and the number of nuclear atoms 5 It may be selected from the group consisting of to 60 heteroaryl groups.
상기 화학식 1a 또는 1b로 표시되는 벤조잔틴계 모이어티(A)에 치환되는 R
4는 당분야에 공지된 통상의 치환기일 수 있으며, 특별히 제한되지 않는다. 일례로, 전술한 R
2 내지 R
3의 정의부와 동일할 수 있다. 또한 R
4의 개수(m)는 특별히 제한되지 않으며, 일례로 0 내지 6의 정수일 수 있다. 여기서 m이 0인 경우 R
4는 수소이며, m이 1 내지 6인 경우 R
4는 수소를 제외한 전술한 치환기를 가질 수 있다. R 4 substituted in the benzoxanthine-based moiety (A) represented by Formula 1a or 1b may be a conventional substituent known in the art, and is not particularly limited. For example, it may be the same as the definition of R 2 to R 3 described above. In addition, the number (m) of R 4 is not particularly limited, and may be an integer of 0 to 6, for example. Here, when m is 0, R 4 is hydrogen, and when m is 1 to 6, R 4 may have the aforementioned substituents other than hydrogen.
본 발명의 일 구체예를 들면, 상기 벤조잔틴계 모이어티(A)는 하기 구조식으로 보다 구체화될 수 있다. For one embodiment of the present invention, the benzoxanthine-based moiety (A) may be further specified by the following structural formula.
전술한 구조식으로 구체화되는 벤조잔틴계 모이어티(A)는 화학식 상에 구체적으로 표시되지 않았으나, 당 분야에 공지된 치환기(예컨대, R
4)가 적어도 하나 이상 치환될 수 있다. Although the benzoxanthine-based moiety (A) embodied in the above-mentioned structural formula is not specifically shown in the formula, at least one or more substituents known in the art (eg, R 4 ) may be substituted.
본 발명의 화학식 1에서, 상기 L의 아릴렌기, 헤테로아릴렌기와; Ar
1 내지 Ar
2, 및 R
1 내지 R
4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
2~C
40의 알케닐기, C
2~C
40의 알키닐기, C
3~C
40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C
1~C
40의 알킬옥시기, C
6~C
60의 아릴옥시기, C
1~C
40의 알킬실릴기, C
6~C
60의 아릴실릴기, C
1~C
40의 알킬보론기, C
6~C
60의 아릴보론기, C
6~C
60의 아릴포스핀기, C
6~C
60의 아릴포스핀옥사이드기, C
6~C
60의 아릴아민기, C
5~C
60의 아릴헤테로아릴아민기, 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. In Formula 1 of the present invention, L is an arylene group or a heteroarylene group; Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 Heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 groups of an alkyl boron, C 6 ~ aryl boronic of C 60, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, C 6 ~ C 60 aryl amine group, C 5 ~ C 60 may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when the substituents are plural, they may be the same or different from each other can
본 발명의 일 실시예를 들면, 상기 화학식 1로 표시되는 화합물은, 벤조잔틴계 모이어티(A)의 종류에 따라 하기 화학식 3 또는 4로 보다 구체화될 수 있다. For an embodiment of the present invention, the compound represented by Chemical Formula 1 may be more specific to the following Chemical Formula 3 or 4 depending on the type of the benzoxanthine-based moiety (A).
상기 화학식 3 또는 4에서, In Formula 3 or 4,
Z
1~Z
3, X, Ar
1~Ar
2, L 및 n은 각각 화학식 1에서 정의된 바와 같다. Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Chemical Formula 1.
본 발명의 다른 일 실시예를 들면, 상기 화학식 3으로 표시되는 화합물은, 벤조잔틴계 코어(core)에 연결되는 링커(L)의 결합위치에 따라 하기 화학식 5 내지 화학식 8 중 어느 하나로 보다 구체화될 수 있다. 그러나 이에 제한되는 것은 아니다. In another embodiment of the present invention, the compound represented by Formula 3 may be more specific to any one of the following Formulas 5 to 8 depending on the bonding position of the linker (L) connected to the benzoxanthine-based core. can However, the present invention is not limited thereto.
상기 화학식 5 내지 8에서, In Formulas 5 to 8,
Z
1~Z
3, X, Ar
1~Ar
2, L 및 n은 각각 화학식 1에서 정의된 바와 같다. Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Chemical Formula 1.
본 발명의 다른 일 실시예를 들면, 상기 화학식 4로 표시되는 화합물은, 벤조잔틴계 코어(core)에 연결되는 링커(L)의 결합위치에 따라 하기 화학식 9 내지 화학식 12 중 어느 하나로 보다 구체화될 수 있다. 그러나 이에 제한되는 것은 아니다. In another embodiment of the present invention, the compound represented by Chemical Formula 4 may be more specific to any one of the following Chemical Formulas 9 to 12 depending on the bonding position of the linker (L) connected to the benzoxanthine-based core. can However, the present invention is not limited thereto.
상기 화학식 9 내지 12에서, In Formulas 9 to 12,
Z
1 ~ Z
3, X, Ar
1 ~ Ar
2, L 및 n은 각각 화학식 1에서 정의된 바와 같다. Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Formula 1.
상기 화학식 3 내지 화학식 12 중 어느 하나로 표시되는 화합물의 바람직한 일례를 들면, Z
1 내지 Z
3 중 2 ~ 3개는 N이며, Ar
1 및 Ar
2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C
6~C
60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택된다. For a preferred example of the compound represented by any one of Formulas 3 to 12, Z 1 to Z 3 are N, and Ar 1 and Ar 2 are the same as or different from each other, and each independently C 6 ~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.
L은 단일결합이거나 또는 C
6~C
18의 아릴렌기이며, n은 1 내지 2의 정수이다. L is a single bond or a C 6 ~ C 18 arylene group, and n is an integer of 1 to 2.
R
1 내지 R
4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C
1~C
40의 알킬기, C
6~C
60의 아릴기, 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택되며, m은 0 내지 6의 정수이다. R 1 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, and 5 to 60 nuclear atoms It is selected from the group consisting of a heteroaryl group, and m is an integer from 0 to 6.
여기서, 상기 L의 아릴렌기; Ar
1 및 Ar
2의 아릴기, 헤테로아릴기; 및 R
1 내지 R
4의 알킬기, 아릴기, 헤테로아릴기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C
1~C
40의 알킬기, C
6~C
60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C
6~C
60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우 이들은 서로 동일하거나 상이할 수 있다.Here, the arylene group of L; Ar 1 and Ar 2 An aryl group, a heteroaryl group; And R 1 To R 4 Alkyl group, aryl group, heteroaryl group is each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, It may be substituted with one or more substituents selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60. In this case, when the substituents are plural, they may be the same or different from each other.
이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물은 하기 예시되는 화합물, 예컨대 1 내지 200으로 표시되는 화합물로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by Formula 1 of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by 1 to 200. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl (alkenyl)" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like.
본 발명에서 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkynyl (alkynyl)" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된탄소수 6 내지 40의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미한다.In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 40 carbon atoms.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" refers to silyl substituted with aryl having 5 to 40 carbon atoms.
본 발명에서 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
<전자수송층 재료><Electron transport layer material>
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 전자수송층을 제공한다. The present invention provides an electron transport layer comprising the compound represented by Formula 1 above.
상기 전자수송층(ETL)은 음극에서 주입되는 전자를 인접하는 층, 구체적으로 발광층으로 이동시키는 역할을 한다. The electron transport layer (ETL) serves to move electrons injected from the cathode to an adjacent layer, specifically, the light emitting layer.
상기 화학식 1로 표시되는 화합물은, 전자수송층(ETL) 재료로서 단독으로 사용될 수 있으며, 또는 당 분야에 공지된 전자수송층 재료와 혼용될 수 있다. 바람직하게는 단독으로 사용되는 것이다. The compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
상기 화학식 1의 화합물과 혼용될 수 있는 전자수송층 재료는, 당 분야에서 통상적으로 공지된 전자수송 물질을 포함한다. 사용 가능한 전자 수송 물질의 비제한적인 예로는 옥사졸계 화합물, 이소옥사졸계 화합물, 트리아졸계 화합물, 이소티아졸(isothiazole)계 화합물, 옥사디아졸계 화합물, 티아다아졸(thiadiazole)계 화합물, 페릴렌(perylene)계 화합물, 알루미늄 착물(예: Alq
3 (트리스(8-퀴놀리놀라토)-알루미늄(tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, 갈륨 착물(예: Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)) 등이 있다. 이들을 단독으로 사용하거나 또는 2종 이상 혼용할 수 있다. The electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compound, aluminum complex (eg, Alq 3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complex (eg, Gaq'2OPiv, Gaq) '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.
본 발명에서, 상기 화학식 1의 화합물과 전자수송층 재료를 혼용할 경우, 이들의 혼합 비율은 특별히 제한되지 않으며, 당 분야에 공지된 범위 내에서 적절히 조절될 수 있다. In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited, and may be appropriately adjusted within a range known in the art.
<전자수송 보조층 재료><Electron transport auxiliary layer material>
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 전자수송 보조층을 제공한다. In addition, the present invention provides an electron transport auxiliary layer including the compound represented by the formula (1).
상기 전자수송층은 발광층과 전자수송층 사이에 배치되어, 상기 발광층에서 생성된 엑시톤 또는 정공이 전자수송층으로 확산되는 것을 방지하는 역할을 한다. The electron transport layer is disposed between the emission layer and the electron transport layer, and serves to prevent the excitons or holes generated in the emission layer from diffusing into the electron transport layer.
상기 화학식 1로 표시되는 화합물은, 전자수송 보조층 재료로서 단독으로 사용될 수 있으며, 또는 당 분야에 공지된 전자수송층 재료와 혼용될 수 있다. 바람직하게는 단독으로 사용되는 것이다. The compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
상기 화학식 1의 화합물과 혼용될 수 있는 전자수송 보조층 재료는, 당 분야에서 통상적으로 공지된 전자수송 물질을 포함한다. 일례로, 상기 전자수송 보조층은 옥사디아졸 유도체, 트리아졸 유도체, 페난트롤린 유도체(예, BCP), 질소를 포함하는 헤테로환 유도체 등을 포함할 수 있다. The electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a nitrogen-containing heterocyclic derivative, and the like.
본 발명에서, 상기 화학식 1의 화합물과 전자수송 보조층 재료를 혼용할 경우, 이들의 혼합 비율은 특별히 제한되지 않으며, 당 분야에 공지된 범위 내에서 적절히 조절될 수 있다. In the present invention, when the compound of Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and may be appropriately adjusted within a range known in the art.
<유기 전계 발광 소자><Organic electroluminescent device>
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) including the compound represented by Formula 1 according to the present invention.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2종 이상 혼합되어 사용될 수 있다.Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above. In this case, the compound may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층(보다 구체적으로, 인광 발광 호스트 재료), 전자수송층, 전자수송 보조층인 것이 바람직하다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer is represented by Formula 1 compounds. Specifically, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer (more specifically, a phosphorescent light emitting host material), an electron transport layer, and an electron transport auxiliary layer.
본 발명에 따른 유기 전계 발광 소자의 발광층은 호스트 재료와 도펀트 재료를 포함하는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. 또한 본 발명의 발광층은 상기 화학식 1의 화합물 이외의 당 분야의 공지된 화합물을 호스트로서 포함할 수 있다.The light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and in this case, the compound of Formula 1 may be included as the host material. In addition, the light emitting layer of the present invention may include a known compound in the art other than the compound of Formula 1 as a host.
상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 전계 발광 소자에 포함되는 것이 바람직하다. 특히, 본 발명의 화학식 1로 표시되는 화합물은 고효율을 가진 발광층의 그린 인광 exciplex N-type 호스트 재료인 것이 바람직하다. When the compound represented by Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic electroluminescent device (luminous efficiency and power efficiency), lifespan, luminance, and driving voltage can be improved. Specifically, the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light emitting layer having high efficiency.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층, 보다 바람직하게는 인광 호스트가 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 한편 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. At this time, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably the light emitting layer, more preferably a phosphorescent host may include a compound represented by Formula 1 above. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.
본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는, 전술한 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당 업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. have.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
본 발명의 유기 전계 발광 소자 제조시 사용되는 기판은 특별히 한정되지 않으며, 일례로 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet may be used.
또, 양극 물질은 당 분야에 공지된 양극 물질을 제한 없이 사용할 수 있다. 일례를 들면, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO
2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, as the cathode material, a cathode material known in the art may be used without limitation. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides 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 or polyaniline; and carbon black, but is not limited thereto.
또, 음극 물질은 당 분야에 공지된 음극 물질을 제한 없이 사용할 수 있다. 일례를 들면, 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, as the negative electrode material, a negative electrode material known in the art may be used without limitation. For example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 공지된 통상의 물질을 제한 없이 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예][Preparation example]
[준비예 1] C-1 의 합성[Preparation Example 1] Synthesis of C-1
[1] 1-(4-브로모-2-플루오로페닐)-8-에톡시나프탈렌 의 합성[1] Synthesis of 1-(4-bromo-2-fluorophenyl)-8-ethoxynaphthalene
(8-에톡시나프탈렌-1일)보로닉산 50.0g 과 4-브로모-2-플루오로-1-아이오도벤젠 59.6g, 테트라키스페닐포스핀팔라듐(0) 13.3g, K
2CO
3 95.5g을 넣고 THF 1L와 물 500mL를 넣고, 24시간 동안 환류 교반하였다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 용액을 분액 깔때기에 옮겨 MC로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 1-(4-브로모-2-플루오로페닐)-8-에톡시나프탈렌 (57.2g, 수율 75%) 얻었다.(8-ethoxynaphthalen-1yl)boronic acid 50.0g, 4-bromo-2-fluoro-1-iodobenzene 59.6g, tetrakisphenylphosphinepalladium(0) 13.3g, K 2 CO 3 95.5 g, 1L of THF and 500 mL of water were added, and the mixture was stirred under reflux for 24 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with MC, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to 1-(4-bromo-2) -Fluorophenyl)-8-ethoxynaphthalene (57.2 g, yield 75%) was obtained.
[2] 8-(4-브로모-2-플루오로페닐)나프탈렌-1-올 의 합성[2] Synthesis of 8- (4-bromo-2-fluorophenyl) naphthalen-1-ol
1-(4-브로모-2-플루오로페닐)-8-에톡시나프탈렌 27.6g, MC 450mL을 넣은 후 0℃로 냉각하고, BBr
3 50g을 첨가하고 상온으로 서서히 올려 24시간 동안 상온 교반하였다. 반응이 종료 되면 -78℃로 냉각한 후 메탄올 600mL을 서서히 적가하고, 충분한 물을 다시 첨가하였다. 용액을 분액 깔때기에 옮겨 MC로 추출하고 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 8-(4-브로모-2-플루오로페닐)나프탈렌-1-올 (49.6g, 수율 97%)을 얻었다.1-(4-bromo-2-fluorophenyl)-8-ethoxynaphthalene 27.6 g, MC 450 mL was added, cooled to 0° C., 50 g of BBr 3 was added, and the mixture was slowly raised to room temperature and stirred at room temperature for 24 hours. . Upon completion of the reaction, after cooling to -78°C, 600 mL of methanol was slowly added dropwise, and sufficient water was added again. The solution was transferred to a separatory funnel, extracted with MC, and the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography. 8-(4-bromo-2-fluorophenyl)naphthalen-1-ol (49.6 g) , yield 97%) was obtained.
[3] C-1 의 합성[3] Synthesis of C-1
상기 8-(4-브로모-2-플루오로페닐)나프탈렌-1-올 49.6g, N-메틸-2-피롤리디논 670mL, K
2CO
3 43.2g을 넣은 후 200℃에서 3시간 환류 교반하였다. 반응 종료 후 상온으로 온도를 냉각하고, 톨루엔 2L을 첨가하고 10분간 교반하였다. 용액에 물을 첨가한 후 분액 깔때기에 옮겨 MC로 추출하고 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 화합물 C-1 (16g, 수율 69%)을 얻었다.49.6 g of the 8-(4-bromo-2-fluorophenyl) naphthalen-1-ol, 670 mL of N-methyl-2-pyrrolidinone, and 43.2 g of K 2 CO 3 were added, followed by stirring under reflux at 200° C. for 3 hours. did. After completion of the reaction, the temperature was cooled to room temperature, 2L of toluene was added, and the mixture was stirred for 10 minutes. After adding water to the solution, it was transferred to a separatory funnel, extracted with MC, and the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain compound C-1 (16 g, yield 69%).
1H-NMR: 8.50 (d, 1H), 8.12 (d, 1H), 7.98 (d, 1H), 7.81 (t, 1H), 7.62-7.34 (m, 4H), 6.43 (d, 2H)1H-NMR: 8.50 (d, 1H), 8.12 (d, 1H), 7.98 (d, 1H), 7.81 (t, 1H), 7.62-7.34 (m, 4H), 6.43 (d, 2H)
Mass : [(M+H)
+] : 298Mass : [(M+H) + ] : 298
[준비예 2] C-2 의 합성[Preparation Example 2] Synthesis of C-2
[1] 8-(4-브로모페닐)나프탈렌-1-일)(메틸)설판 의 합성[1] Synthesis of 8- (4-bromophenyl) naphthalen-1-yl) (methyl) sulfane
상기 준비예1-[1] 에서 (8-에톡시나프탈렌-1일)보로닉산 대신 (8-아이오도나프탈렌-1-일)설판 을 사용한 것을 제외하고는, 동일한 방법으로 8-(4-브로모페닐)나프탈렌-1-일)(메틸)설판 (50.1g, 수율 76%)를 제조하였다.8-(4-bromine) in the same manner as in Preparation Example 1-[1], except that (8-iodonaphthalen-1-yl)sulfane was used instead of (8-ethoxynaphthalen-1-yl)boronic acid. Mophenyl)naphthalen-1-yl)(methyl)sulfane (50.1 g, yield 76%) was prepared.
[2] 1-(4-브로모페닐)-8-(메틸설피닐)나프탈렌 의 합성[2] Synthesis of 1-(4-bromophenyl)-8-(methylsulfinyl)naphthalene
질소 대기상태의 아세토나이트릴 용액 800mL에 8-(4-브로모페닐)나프탈렌-1-일)(메틸)설판 50.1g 과 V
2O
5 2.8g을 첨가한 후, 0℃로 온도를 낮추고 H
2O
2 수용액 20.9mL(33%) 을 넣은 후 10℃에서 1시간 교반하였다. 반응이 종료되면, 반응물에 물 1L를 추가하고 상온으로 천천히 온도를 올린 후 에틸 아세테이트 1.5L를 이용하여 추출한다. 유기층을 황산마그네슘으로 건조시킨 후, 농축하여 1-(4-브로모페닐)-8-(메틸설피닐)나프탈렌 (41.2g, 수율 83%)을 얻었다.After adding 50.1 g of 8-(4-bromophenyl)naphthalen-1-yl)(methyl)sulfane and 2.8g of V 2 O 5 to 800 mL of an acetonitrile solution in a nitrogen atmosphere, lower the temperature to 0°C and H 20.9 mL (33%) of 2 O 2 aqueous solution was added and stirred at 10° C. for 1 hour. When the reaction is completed, 1 L of water is added to the reaction mass, and the temperature is slowly raised to room temperature, followed by extraction using 1.5 L of ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to obtain 1-(4-bromophenyl)-8-(methylsulfinyl)naphthalene (41.2 g, yield 83%).
[3] C-2 의 합성[3] Synthesis of C-2
H
2SO
4 130mL 을 0℃로 냉각 후 1-(4-브로모페닐)-8-(메틸설피닐)나프탈렌 41.2g을 천천히 투입하였다. 이후 25℃에서 2시간 동안 교반하고, 물 1L 를 넣어준 후, K
2CO
3 수용액으로 반응물의 pH를 pH 8로 맞추었다. 반응물을 에틸 아세테이트를 이용하여 추출한 후 얻어진 유기층을 황산마그네슘으로 건조시킨 후, 컬럼 크로마토 그래피로 정제하여 C-2 (26.2g, 수율 35%) 을 얻었다.After cooling 130 mL of H 2 SO 4 to 0° C., 41.2 g of 1-(4-bromophenyl)-8-(methylsulfinyl)naphthalene was slowly added thereto. After stirring at 25° C. for 2 hours, 1 L of water was added, and the pH of the reactant was adjusted to pH 8 with an aqueous K 2 CO 3 solution. The reaction product was extracted with ethyl acetate, and the resulting organic layer was dried over magnesium sulfate and purified by column chromatography to obtain C-2 (26.2 g, yield 35%).
1H-NMR: 8.50 (d, 1H), 8.06 (d, 1H), 7.94 (d, 1H), 7.77 (t, 1H), 7.56 (s, 1H), 7.48-7.34 (m, 5H)1H-NMR: 8.50 (d, 1H), 8.06 (d, 1H), 7.94 (d, 1H), 7.77 (t, 1H), 7.56 (s, 1H), 7.48-7.34 (m, 5H)
Mass : [(M+H)
+] : 314Mass : [(M+H) + ] : 314
[준비예 3] C-3 의 합성[Preparation Example 3] Synthesis of C-3
[1] 메틸-8-(-3-브로모페닐)-1-나프토에이트 의 합성[1] Synthesis of methyl-8-(-3-bromophenyl)-1-naphthoate
(8-(메톡시카보닐)나프탈렌-1-일)보로닉산 50.0 g, 1-브로모-3-아이오도벤젠 55g, 테트라키스페닐포스핀팔라듐(0) 10.9g, K
2CO
3 50.1g, THF 1L, 물 250mL를 넣고, 24시간 동안 환류 교반하였다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 용액을 분액 깔때기에 옮겨 MC로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 메틸-8-(-3-브로모페닐)-1-나프토에이트 (51.2g, 수율 77%)를 얻었다.(8-(methoxycarbonyl)naphthalen-1-yl)boronic acid 50.0 g, 1-bromo-3-iodobenzene 55g, tetrakisphenylphosphine palladium (0) 10.9g , K 2 CO 3 50.1 g , THF 1L, water 250mL was added, and the mixture was stirred under reflux for 24 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with MC, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to methyl-8-(-3-bromine) Mophenyl)-1-naphthoate (51.2 g, yield 77%) was obtained.
[2] 10-브로모-7H-벤조[de]안트라센-7온 의 합성[2] Synthesis of 10-bromo-7H-benzo [de] anthracen-7one
메틸-8-(-3-브로모페닐)-1-나프토에이트 51.2g 를 Methanesulfonic acid 500mL에 녹이고 상온에서 교반하였다. 반응이 완료되면 0℃까지 냉각시킨 후 물을 첨가하여 석출된 고체를 여과한 뒤, MC에 녹여 황산마그네슘으로 건조시킨 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 10-브로모-7H-벤조[de]안트라센-7온 (34.0g, 수율 64%)을 얻었다.51.2 g of methyl-8-(-3-bromophenyl)-1-naphthoate was dissolved in 500 mL of methanesulfonic acid and stirred at room temperature. When the reaction is complete, the reaction is cooled to 0° C., water is added, the precipitated solid is filtered, dissolved in MC, dried over magnesium sulfate, and the resulting compound is purified by column chromatography to 10-bromo-7H-benzo [ de]anthracene-7one (34.0 g, yield 64%) was obtained.
[3] 10-브로모-7H-벤조[de]안트라센 의 합성[3] Synthesis of 10-bromo-7H-benzo [de] anthracene
10-브로모-7H-벤조[de]안트라센-7온 34.0g을 에틸렌 글리콜 500mL에 녹인 후에 hydrazine monohydrate 150g, KOH 15g을 첨가한 후, 185℃에서 교반하였다. 반응이 완료되면 0℃까지 낮추고 물을 넣어준 뒤, 고체로 석출된 것을 여과하여 소량의 물로 세척하였다. MC 에 다시 녹여 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 생성물 10-브로모-7H-벤조[de]안트라센 (29.1g, 수율 95%)을 얻었다.After dissolving 34.0 g of 10-bromo-7H-benzo [de] anthracene-7one in 500 mL of ethylene glycol, 150 g of hydrazine monohydrate and 15 g of KOH were added, followed by stirring at 185 °C. When the reaction was completed, the temperature was lowered to 0° C., water was added, and the precipitated solid was filtered and washed with a small amount of water. After re-dissolving in MC, drying over magnesium sulfate, and concentration, the resulting compound was purified by column chromatography to obtain the product 10-bromo-7H-benzo [de] anthracene (29.1 g, yield 95%).
[4] C-3 의 합성[4] Synthesis of C-3
둥근바닥플라스크에 상기 합성에서 얻어진 10-브로모-7H-벤조[de]안트라센 29.1g, KOt-Bu 30g, DMF 1L에 녹인 후 0℃에서 5분 동안 교반시키고 상온으로 올려서 iodomethane 40g을 첨가하였다. 반응이 완료되면 MC와 물로 추출한 후 유기층을 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 화합물 C-3 (28.4g, 수율 90%)을 얻었다.In a round-bottom flask, 29.1 g of 10-bromo-7H-benzo [de] anthracene obtained in the above synthesis, 30 g of KOt-Bu, and 1 L of DMF were dissolved, stirred at 0° C. for 5 minutes, and then raised to room temperature, and 40 g of iodomethane was added. Upon completion of the reaction, the mixture was extracted with MC and water, the organic layer was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain compound C-3 (28.4 g, yield 90%).
[준비예 4] C-4 의 합성[Preparation Example 4] Synthesis of C-4
[1] 7-([1,1`-바이페닐]-2-일)-10-브로모-7H-벤조[de]안트라센-7-올 의 합성[1] Synthesis of 7-([1,1`-biphenyl]-2-yl)-10-bromo-7H-benzo [de] anthracen-7-ol
질소 대기상태의 플라스크에 2-아이오도-1,1`-바이페닐 20g과 THF 250mL를 넣고 -78℃로 냉각 교반시켰다. 그 후 2.5M n-부틸리튬을 30.5mL을 천천히 적가하였다. 30분 후 상기 10-브로모-7H-벤조[de]안트라센-7-온 21.5g을 무수 THF 100mL에 녹여 천천히 넣어준 후, 상온에서 3시간 교반하였다. 반응이 종료되면 물 250mL를 넣어 반응을 종료하고 MC 로 추출한 후 얻어진 유기층을 황산 마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 생성물 7-([1,1`-바이페닐]-2-일)-10-브로모-7H-벤조[de]안트라센-7-올 (23.5g, 순도 74%)을 얻었다.20 g of 2-iodo-1,1`-biphenyl and 250 mL of THF were placed in a flask under nitrogen atmosphere, and the mixture was cooled and stirred at -78°C. After that, 30.5 mL of 2.5M n-butyllithium was slowly added dropwise. After 30 minutes, 21.5 g of the 10-bromo-7H-benzo [de] anthracen-7-one was dissolved in 100 mL of anhydrous THF and slowly added thereto, followed by stirring at room temperature for 3 hours. When the reaction is complete, 250 mL of water is added to terminate the reaction, and the organic layer obtained after extraction with MC is dried over magnesium sulfate, concentrated, and the resulting compound is purified by column chromatography to obtain product 7-([1,1`-biphenyl] -2-yl)-10-bromo-7H-benzo [de] anthracen-7-ol (23.5 g, purity 74%) was obtained.
[2] C-4 의 합성[2] Synthesis of C-4
플라스크에 7-([1,1`-바이페닐]-2-일)-10-브로모-7H-벤조[de]안트라센-7-올 23.5g 과 아세트산 200mL, HCl 5.4mL을 넣고 환류 교반하였다. 반응이 끝나면 상온으로 식히고 물 270mL을 넣고 생성된 고체를 여과하였다. 고체를 물과 MC로 추출하여 얻어진 유기층을 황산마그네슘으로 건조하고 농축한 후 생성된 화합물을 컬럼 크로마토그래피로 정제하여 화합물 C-4 (17.9g, 수율 76%)을 얻었다.23.5 g of 7-([1,1`-biphenyl]-2-yl)-10-bromo-7H-benzo [de] anthracen-7-ol, 200 mL of acetic acid, and 5.4 mL of HCl were added to the flask and stirred under reflux. . After the reaction was completed, it was cooled to room temperature, 270 mL of water was added, and the resulting solid was filtered. The organic layer obtained by extracting the solid with water and MC was dried over magnesium sulfate, concentrated, and the resulting compound was purified by column chromatography to obtain compound C-4 (17.9 g, yield 76%).
1H-NMR: 8.50 (d, 1H), 8.06 (d, 1H), 8.03 (d, 1H), 7.91 (d, 3H), 7.74 (t, 1H), 7.55 (d, 2H), 7.44-7.30 (m, 7H), 6.50 (d, 1H)1H-NMR: 8.50 (d, 1H), 8.06 (d, 1H), 8.03 (d, 1H), 7.91 (d, 3H), 7.74 (t, 1H), 7.55 (d, 2H), 7.44-7.30 ( m, 7H), 6.50 (d, 1H)
Mass : [(M+H)
+] : 446Mass : [(M+H) + ] : 446
[합성예][Synthesis Example]
[합성예 1] 화합물 6 의 합성[Synthesis Example 1] Synthesis of compound 6
2,4-다이페닐-6-(3-(4,4,5,5-테트라메틸-1,3,2-다이옥사보로란-2-일)-1,3,5-트리아진 5.0g 및 C-1 3.3g, 테트라키스페닐포스핀팔라듐(0) 0.7g, K
2CO
3 4.6g을 톨루엔 100ml, 에탄올 20ml, 물 20ml에 넣고 2시간 가열 환류 교반하였다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 용액을 분액 깔때기에 옮겨 MC로 추출하고, 용액을 분액 깔때기에 옮겨서 메틸렌클로아이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 화합물 6 (3.8g, 수율 65%)을 얻었다.5.0 g of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,5-triazine And 3.3 g of C-1, 0.7 g of tetrakisphenylphosphine palladium (0), and 4.6 g of K 2 CO 3 were placed in 100 ml of toluene, 20 ml of ethanol, and 20 ml of water, and heated and stirred under reflux for 2 hours. was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with MC, the solution was transferred to a separatory funnel, extracted with methylene chloride, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 6 ( 3.8 g, yield 65%) was obtained.
Mass : [(M+H)
+] : 526Mass : [(M+H) + ] : 526
[합성예 2] 화합물 13 의 합성[Synthesis Example 2] Synthesis of compound 13
4-([1,1`-바이페닐]-4-일)-2-페닐-6-(4-(4,4,5,5-테트라메틸-1,3,2-다이옥사보로란-2-일)페닐)피리미딘 5.0g 및 C-1 2.9g, 테트라키스페닐포스핀팔라듐(0) 0.7g, K
2CO
3 4.6g을 톨루엔 100ml, 에탄올 20ml, 물 20ml에 넣고 2시간 가열 환류 교반하였다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 용액을 분액 깔때기에 옮겨서 메틸렌클로아이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 화합물 13 (3.9g, 수율 67%)을 얻었다.4-([1,1`-biphenyl]-4-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- 2- yl) phenyl) pyrimidine and 5.0g C-1 2.9g, tetrakis triphenylphosphine palladium (0) 0.7g, K 2 CO 3 4.6g put in 100ml of toluene, 20ml of ethanol, 20ml of water 2 time heating reflux stirred. When the reaction was completed, the temperature of the reactant was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with methylene chloride, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 13 (3.9 g, yield) 67%) was obtained.
Mass : [(M+H)
+] : 601Mass : [(M+H) + ] : 601
[합성예 3] 화합물 16 의 합성[Synthesis Example 3] Synthesis of compound 16
2,4-다이페닐-6-(4`-(4,4,5,5-테트라메틸-1,3,2-다이옥사보로란-2-일)-[1,1`-바이페닐]-4-일)-1,3,5-트리아진 5.0g 및 C-1 2.9g, 테트라키스페닐포스핀팔라듐(0) 0.7g, K
2CO
3 4.6g을 톨루엔 100ml, 에탄올 20ml, 물 20ml에 넣고 2시간 가열 환류 교반하였다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 용액을 분액 깔때기에 옮겨서 메틸렌클로아이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 화합물 16 (4.2g, 수율 71%)을 얻었다.2,4-diphenyl-6-(4`-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1`-biphenyl] -4-yl) -1,3,5-triazine 5.0 g and C-1 2.9 g, tetrakisphenylphosphine palladium (0) 0.7 g, K 2 CO 3 4.6 g 100 ml toluene, 20 ml ethanol, 20 ml water and stirred under reflux for 2 hours. Upon completion of the reaction, the temperature of the reactant was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with methylene chloride, and the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 16 (4.2 g, yield). 71%) was obtained.
Mass : [(M+H)
+] : 602Mass : [(M+H) + ] : 602
[합성예 4] 화합물 18 의 합성[Synthesis Example 4] Synthesis of compound 18
2-([1,1`-바이페닐]-4-일)-4-페닐-6-(3`-(4,4,5,5-테트라메틸-1,3,2-다이옥사보로란-2-일)-[1,1`-바이페닐]-4-일)-1,3,5-트리아진 5.0g 및 C-1 2.5g, 테트라키스페닐포스핀팔라듐(0) 0.7g, K
2CO
3 4.6g을 톨루엔 100ml, 에탄올 20ml, 물 20ml에 넣고 2시간 가열 환류 교반하였다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 용액을 분액 깔때기에 옮겨서 메틸렌클로아이드로 추출하고, 유기층을 황산마그네슘으로 건조시킨 후, 농축하고, 컬럼 크로마토그래피로 정제하여 화합물 16 (3.7g, 수율 65%)을 얻었다.2-([1,1`-biphenyl]-4-yl)-4-phenyl-6-(3`-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) -2-yl)-[1,1`-biphenyl]-4-yl)-1,3,5-triazine 5.0g and C-1 2.5g, tetrakisphenylphosphinepalladium (0) 0.7g, K 2 CO 3 4.6g was put into 100ml of toluene, 20ml of ethanol, and 20ml of water, and the mixture was heated and stirred under reflux for 2 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, the solution was transferred to a separatory funnel, extracted with methylene chloride, the organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 16 (3.7 g, yield) 65%) was obtained.
Mass : [(M+H)
+] : 602Mass : [(M+H) + ] : 602
[합성예 5] 화합물 31 의 합성[Synthesis Example 5] Synthesis of compound 31
C-1 대신 C-2 를 사용한 것을 제외하고는, 상기 합성예 1 과 동일한 방법을 수행하여 화합물 31 (4.1g, 수율 69%)를 제조하였다.Compound 31 (4.1 g, yield 69%) was prepared in the same manner as in Synthesis Example 1, except that C-2 was used instead of C-1.
Mass : [(M+H)
+] : 542Mass : [(M+H) + ] : 542
[합성예 6] 화합물 38 의 합성[Synthesis Example 6] Synthesis of compound 38
C-1 대신 C-2 를 사용한 것을 제외하고는, 상기 합성예 2와 동일한 방법을 수행하여 화합물 38 (3.9g, 수율 66%)를 제조하였다.Compound 38 (3.9 g, yield 66%) was prepared in the same manner as in Synthesis Example 2, except that C-2 was used instead of C-1.
Mass : [(M+H)
+] : 618Mass : [(M+H) + ] : 618
[합성예 7] 화합물 41 의 합성[Synthesis Example 7] Synthesis of compound 41
C-1 대신 C-2 를 사용한 것을 제외하고는, 상기 합성예 3 과 동일한 방법으로 화합물 41 (3.4g, 수율 62%)를 제조하였다.Compound 41 (3.4 g, yield 62%) was prepared in the same manner as in Synthesis Example 3, except that C-2 was used instead of C-1.
Mass : [(M+H)
+] : 619Mass : [(M+H) + ] : 619
[합성예 8] 화합물 43 의 합성[Synthesis Example 8] Synthesis of compound 43
C-1 대신 C-2 를 사용한 것을 제외하고는, 상기 합성예 4와 동일한 방법으로 화합물 43 (3.8g, 수율 61%)를 제조하였다.Compound 43 (3.8 g, yield 61%) was prepared in the same manner as in Synthesis Example 4, except that C-2 was used instead of C-1.
Mass : [(M+H)
+] : 695Mass : [(M+H) + ] : 695
[합성예 9] 화합물 56 의 합성[Synthesis Example 9] Synthesis of compound 56
상기 합성예 1 에서 C-1 대신 C-3 를 사용한 것을 제외하고는 동일한 방법으로 화합물 56 (4.2g, 수율 65%)를 제조하였다.Compound 56 (4.2 g, yield 65%) was prepared in the same manner as in Synthesis Example 1, except that C-3 was used instead of C-1.
Mass : [(M+H)
+] : 552Mass : [(M+H) + ] : 552
[합성예 10] 화합물 63 의 합성[Synthesis Example 10] Synthesis of compound 63
C-1 대신 C-3 를 사용한 것을 제외하고는, 상기 상기 합성예 2와 동일한 방법으로 화합물 63 (3.7g, 수율 66%)를 제조하였다.Compound 63 (3.7 g, yield 66%) was prepared in the same manner as in Synthesis Example 2, except that C-3 was used instead of C-1.
Mass : [(M+H)
+] : 628Mass : [(M+H) + ] : 628
[합성예 11] 화합물 66 의 합성[Synthesis Example 11] Synthesis of compound 66
C-1 대신 C-3을 사용한 것을 제외하고는, 상기 합성예 3 과 동일한 방법으로 화합물 66 (3.6g, 수율 64%)를 제조하였다.Compound 66 (3.6 g, yield 64%) was prepared in the same manner as in Synthesis Example 3, except that C-3 was used instead of C-1.
Mass : [(M+H)
+] : 629Mass : [(M+H) + ] : 629
[합성예 12] 화합물 68 의 합성[Synthesis Example 12] Synthesis of compound 68
C-1 대신 C-3을 사용한 것을 제외하고는, 상기 합성예 4와 동일한 방법으로 화합물 68 (3.9g, 수율 62%)를 제조하였다.Compound 68 (3.9 g, yield 62%) was prepared in the same manner as in Synthesis Example 4, except that C-3 was used instead of C-1.
Mass : [(M+H)
+] : 705Mass : [(M+H) + ] : 705
[합성예 13] 화합물 181 의 합성[Synthesis Example 13] Synthesis of compound 181
C-1 대신 C-4를 사용한 것을 제외하고는, 상기 합성예 1 과 동일한 방법으로 화합물 56 (5.0g, 수율 65%)를 제조하였다.Compound 56 (5.0 g, yield 65%) was prepared in the same manner as in Synthesis Example 1, except that C-4 was used instead of C-1.
Mass : [(M+H)
+] : 675Mass : [(M+H) + ] : 675
[합성예 14] 화합물 188 의 합성[Synthesis Example 14] Synthesis of compound 188
C-1 대신 C-4를 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 방법으로 화합물 63 (4.3g, 수율 67%)를 제조하였다.Compound 63 (4.3 g, yield 67%) was prepared in the same manner as in Synthesis Example 2, except that C-4 was used instead of C-1.
Mass : [(M+H)
+] : 750Mass : [(M+H) + ] : 750
[합성예 15] 화합물 191 의 합성[Synthesis Example 15] Synthesis of compound 191
C-1 대신 C-4를 사용한 것을 제외하고는, 상기 합성예 3과 동일한 방법으로 화합물 191 (3.3g, 수율 59%)를 제조하였다.Compound 191 (3.3 g, yield 59%) was prepared in the same manner as in Synthesis Example 3, except that C-4 was used instead of C-1.
Mass : [(M+H)
+] : 751Mass : [(M+H) + ] : 751
[합성예 16] 화합물 193 의 합성[Synthesis Example 16] Synthesis of compound 193
C-1 대신 C-4를 사용한 것을 제외하고는, 상기 합성예 4 와 동일한 방법으로 화합물 193 (4.4g, 수율 63%)를 제조하였다.Compound 193 (4.4 g, yield 63%) was prepared in the same manner as in Synthesis Example 4, except that C-4 was used instead of C-1.
Mass : [(M+H)
+] : 827Mass : [(M+H) + ] : 827
[실시예 1 내지 8] 청색 유기 전계 발광 소자의 제작[Examples 1 to 8] Fabrication of a blue organic electroluminescent device
합성예에서 합성된 화합물 6, 13, 16, 18, 31, 38, 41, 43을 각각 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.Compounds 6, 13, 16, 18, 31, 38, 41, and 43 synthesized in Synthesis Example were each subjected to high-purity sublimation purification by a known method, and then a blue organic electroluminescent device was manufactured as follows.
먼저 ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After cleaning with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech) The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (㈜두산전자, 30nm)/화합물 6, 13, 16, 18, 31, 41, 43, 56 각각의 화합물 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics, 30 nm)/Compound 6, 13, 16, 18 , 31, 41, 43, 56 were laminated in the order of each compound (30 nm)/LiF (1 nm)/Al (200 nm) to fabricate an organic electroluminescent device.
한편 상기 실시예 1 내지 8 및 비교예 1 내지 4 에서 사용된 NPB, AND 및 Alq3, 화합물 A-1 및 A-2의 구조는 각각 하기와 같다.Meanwhile, the structures of NPB, AND and Alq3, and compounds A-1 and A-2 used in Examples 1 to 8 and Comparative Examples 1 to 4 are as follows, respectively.
[비교예 1] 청색 유기 전계 발광 소자의 제작[Comparative Example 1] Fabrication of a blue organic electroluminescent device
전자 수송층 재료로서 화합물 6 대신 Alq
3을 사용하는 것을 제외하고는, 상기 실시예 1 과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound 6 as the electron transport layer material.
[비교예 2] 청색 유기 전계 발광 소자의 제작[Comparative Example 2] Fabrication of a blue organic electroluminescent device
전자 수송층 재료를 비(非)포함하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the electron transport layer material was not included.
[비교예 3] 청색 유기 전계 발광 소자의 제작[Comparative Example 3] Fabrication of a blue organic electroluminescent device
전자 수송층 재료로서 화합물 6 대신 화합물 A-1를 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 was used instead of Compound 6 as the electron transport layer material.
[비교예 4] 청색 유기 전계 발광 소자의 제작[Comparative Example 4] Fabrication of a blue organic electroluminescent device
전자 수송층 재료로서 화합물 6 대신 화합물 A-2를 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-2 was used instead of Compound 6 as the electron transport layer material.
[평가예 1][Evaluation Example 1]
실시예 1 내지 8 및 비교예 1 내지 4 에서 각각 제작한 청색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.For the blue organic electroluminescent devices fabricated in Examples 1 to 8 and Comparative Examples 1 to 4, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. indicated.
| 샘플Sample |
전자 수송층
재료electron transport layer material |
구동전압
(V)drive voltage (V) |
발광피크
(nm)luminescence peak (nm) |
전류효율
(cd/A)current efficiency (cd/A) |
| 실시예 1Example 1 | 화합물 6compound 6 | 2.92.9 | 454454 | 7.97.9 |
| 실시예 2Example 2 | 화합물 13compound 13 | 3.13.1 | 455455 | 8.08.0 |
| 실시예 3Example 3 | 화합물 16compound 16 | 3.43.4 | 454454 | 7.57.5 |
| 실시예 4Example 4 | 화합물 18compound 18 | 3.33.3 | 454454 | 8.08.0 |
| 실시예 5Example 5 | 화합물 31compound 31 | 3.53.5 | 455455 | 8.18.1 |
| 실시예 6Example 6 | 화합물 38compound 38 | 3.43.4 | 454454 | 8.28.2 |
| 실시예 7Example 7 | 화합물 41compound 41 | 3.43.4 | 455455 | 8.88.8 |
| 실시예 8Example 8 | 화합물 43compound 43 | 3.33.3 | 455455 | 8.28.2 |
| 비교예 1Comparative Example 1 | Alq 3 Alq 3 | 4.64.6 | 457457 | 5.65.6 |
| 비교예 2Comparative Example 2 | -- | 4.74.7 | 459459 | 6.16.1 |
| 비교예 3Comparative Example 3 | A-1A-1 | 4.44.4 | 459459 | 5.95.9 |
| 비교예 4Comparative Example 4 | A-2A-2 | 4.84.8 | 456456 | 5.25.2 |
상기 표 1에 나타낸 바와 같이, 본 발명의 화합물을 전자 수송층 재료로 사용한 실시예 1 내지 8의 청색 유기 전계 발광 소자는, 종래 Alq
3를 전자 수송층 재료로 사용하는 비교예 1의 청색 유기 전계 발광 소자; 및 전자 수송층을 비포함하는 비교예 2의 청색 유기 전계 발광 소자에 비해 구동전압, 발광피크 및 전류효율 면에서 보다 현저히 우수한 성능을 나타내는 것을 알 수 있었다.또한, 축합된 형태의 안트라센 구조를 갖는 화합물을 전자수송층 재료로 사용하는 실시예 1 내지 8의 청색 유기 전계 발광 소자는, 종래 디벤조계 모이어티와 플루오렌기를 갖는 전자수송층 재료를 포함하는 비교예 3, 및 아진기를 비포함하는 전자수송층 재료를 포함하는 비교예 4의 청색 유기 전계 발광 소자에 비해 구동전압, 발광피크 및 전류효율 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 8 using the compound of the present invention as an electron transport layer material, the blue organic electroluminescent device of Comparative Example 1 using Alq 3 as an electron transport layer material in the prior art ; And it was found that the blue organic EL device of Comparative Example 2 not including an electron transport layer exhibits significantly superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic EL device of Comparative Example 2. In addition, the compound having a condensed anthracene structure The blue organic electroluminescent devices of Examples 1 to 8 using as an electron transport layer material, Comparative Example 3 comprising an electron transport layer material having a conventional dibenzo-based moiety and a fluorene group, and an electron transport layer material without an azine group It was found that compared to the blue organic electroluminescent device of Comparative Example 4 including
[실시예 9 내지 16] 청색 유기 전계 발광 소자의 제작[Examples 9 to 16] Fabrication of a blue organic electroluminescent device
합성예에서 합성된 화합물 56, 63, 66, 68, 181, 188, 191, 193을 각각 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 청색 유기 전계 발광 소자를 제작하였다.Compounds 56, 63, 66, 68, 181, 188, 191, and 193 synthesized in Synthesis Example were each purified by sublimation with high purity by a conventionally known method, and then a blue organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is performed and dried, transferred to a UV OZONE washer (Power sonic 405, Hwashin Tech), and then the substrate is washed using UV for 5 minutes and transferred the substrate to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (㈜두산전자, 30nm)/ 화합물 78, 79, 83, 91, 94, 99, 136, 138, 142 (5 nm)/Alq
3 (25 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics Co., Ltd. 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm)/ Compounds 78, 79, 83, 91, 94, 99, 136, 138, 142 (5 nm)/Alq 3 (25 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.
[비교예 5] 청색 유기 전계 발광 소자의 제조[Comparative Example 5] Preparation of blue organic electroluminescent device
전자수송 보조층 재료로서 화합물 56을 사용하지 않고, 전자수송층 재료인 Alq
3를 25 nm 대신 30 nm로 증착한 것을 제외하고는, 상기 실시예 9와 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound 56 was not used as an electron transport auxiliary layer material, and Alq 3, an electron transport layer material, was deposited at 30 nm instead of 25 nm. .
[비교예 6] 청색 유기 전계 발광 소자의 제작[Comparative Example 6] Fabrication of a blue organic electroluminescent device
전자수송 보조층 재료로서 화합물 56 대신 화합물 A-1를 사용하는 것을 제외하고는, 상기 실시예 9와 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound A-1 was used instead of Compound 56 as an electron transport auxiliary layer material.
[비교예 7] 청색 유기 전계 발광 소자의 제작[Comparative Example 7] Fabrication of a blue organic electroluminescent device
전자수송 보조층 재료로서 화합물 56 대신 화합물 A-2 를 사용하는 것을 제외하고는, 상기 실시예 9와 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound A-2 was used instead of Compound 56 as an electron transport auxiliary layer material.
[평가예 2][Evaluation Example 2]
실시예 9 내지 16 및 비교예 5 내지 7 에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 발광파장, 전류효율을 측정하였고, 그 결과를 하기 표 2에 나타내었다.For the organic electroluminescent devices prepared in Examples 9 to 16 and Comparative Examples 5 to 7, respectively, the driving voltage, the emission wavelength, and the current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. It was.
| 샘플Sample |
전자수송 보조층
재료electron transport auxiliary layer material |
구동 전압
(V)drive voltage (V) |
발광피크
(nm)luminescence peak (nm) |
전류효율
(cd/A)current efficiency (cd/A) |
| 실시예 9Example 9 | 화합물 56compound 56 | 3.13.1 | 454454 | 8.08.0 |
| 실시예 10Example 10 | 화합물 63compound 63 | 3.03.0 | 454454 | 8.18.1 |
| 실시예 11Example 11 | 화합물 66compound 66 | 3.23.2 | 454454 | 8.28.2 |
| 실시예 12Example 12 | 화합물 68compound 68 | 3.13.1 | 454454 | 8.18.1 |
| 실시예 13Example 13 | 화합물 181compound 181 | 3.13.1 | 454454 | 8.08.0 |
| 실시예 14Example 14 | 화합물 188compound 188 | 3.23.2 | 454454 | 8.18.1 |
| 실시예 15Example 15 | 화합물 191compound 191 | 3.13.1 | 455455 | 8.28.2 |
| 실시예 16Example 16 | 화합물 193compound 193 | 3.23.2 | 454454 | 8.38.3 |
| 비교예 5Comparative Example 5 | -- | 4.74.7 | 459459 | 6.16.1 |
| 비교예 6Comparative Example 6 | A-1A-1 | 4.34.3 | 459459 | 5.95.9 |
| 비교예 7Comparative Example 7 | A-2A-2 | 4.84.8 | 455455 | 5.35.3 |
상기 표 2에 나타낸 바와 같이, 본 발명의 화합물을 전자수송 보조층 재료로 사용한 실시예 9 내지 16의 청색 유기 전계 발광 소자는 전자수송 보조층을 비포함하는 비교예 5의 청색 유기 전계 발광 소자에 비해 전류 효율, 발광피크 면에서 우수한 성능을 나타냈으며, 특히 구동전압 면에서 현저히 우수한 성능을 나타내는 것을 알 수 있었다.또한, 축합된 형태의 안트라센 구조를 갖는 화합물을 전자수송 보조층 재료로 사용한 실시예 9 내지 16의 청색 유기 전계 발광 소자는, 종래 디벤조계 모이어티와 플루오렌기를 갖는 전자수송 보조층 재료를 포함하는 비교예 6, 및 아진기를 비포함하는 전자수송층 재료를 포함하는 비교예 7의 청색 유기 전계 발광 소자에 비해 구동전압, 발광피크 및 전류효율 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 2, the blue organic electroluminescent devices of Examples 9 to 16 using the compound of the present invention as an electron transport auxiliary layer material were the blue organic electroluminescent devices of Comparative Example 5 without an electron transport auxiliary layer. Compared to that, it showed excellent performance in terms of current efficiency and luminescence peak, and particularly in terms of driving voltage. In addition, an example in which a compound having a condensed anthracene structure was used as an electron transport auxiliary layer material The blue organic electroluminescent devices of 9 to 16 are of Comparative Example 6 including an electron transport auxiliary layer material having a conventional dibenzo-based moiety and a fluorene group, and Comparative Example 7 including an electron transport layer material not including an azine group It was found that the blue organic EL device exhibited superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic EL device.
Claims (18)
- 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,Z 1 내지 Z 3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C(R 1) 또는 N이고, 다만 Z 1 내지 Z 3 중 적어도 2개는 N이며, Z 1 To Z 3 Are the same as or different from each other, and each independently C(R 1 ) or N, provided that at least two of Z 1 To Z 3 are N,Ar 1 및 Ar 2는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C 1~C 40의 알킬기, C 2~C 40의 알케닐기, C 2~C 40의 알키닐기, C 3~C 40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C 6~C 60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C 1~C 40의 알킬옥시기, C 6~C 60의 아릴옥시기, C 3~C 40의 알킬실릴기, C 6~C 60의 아릴실릴기, C 1~C 40의 알킬보론기, C 6~C 60의 아릴보론기, C 6~C 60의 아릴포스파닐기, C 6~C 60의 모노아릴포스피닐기, C 6~C 60의 디아릴포스피닐기, C 6~C 60의 아릴아민기, C 5~C 60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택되며, Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl Boron group, C 6 ~ C 60 Arylphosphanyl group, C 6 ~ C 60 Monoarylphosphinyl group, C 6 ~ C 60 Diarylphosphinyl group, C 6 ~ C 60 Arylamine group, C 5 ~ C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms,L은 단일결합이거나, 또는 C 6~C 18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고, L is a single bond, or is selected from the group consisting of a C 6 ~ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,A는 하기 화학식 1a 또는 화학식 1b 중 어느 하나로 표시되는 치환기이며,A is a substituent represented by any one of Formula 1a or Formula 1b,[화학식 1a][Formula 1a]
[화학식 1b][Formula 1b]
상기 화학식 1a 또는 1b에서, In Formula 1a or 1b,*는 상기 화학식 1에 결합되는 부분을 의미하고, * means a moiety bonded to Formula 1,X는 단일결합이거나 또는 O, S 및 CR 2R 3로 이루어진 군에서 선택되며,X is a single bond or is selected from the group consisting of O, S and CR 2 R 3 ,n은 0 내지 3의 정수이며, m은 0 내지 6의 정수이며,n is an integer from 0 to 3, m is an integer from 0 to 6,R 1 내지 R 4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C 1~C 40의 알킬기, C 2~C 40의 알케닐기, C 2~C 40의 알키닐기, C 3~C 40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C 6~C 60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C 1~C 40의 알킬옥시기, C 6~C 60의 아릴옥시기, C 3~C 40의 알킬실릴기, C 6~C 60의 아릴실릴기, C 1~C 40의 알킬보론기, C 6~C 60의 아릴보론기, C 6~C 60의 아릴포스파닐기, C 6~C 60의 모노아릴포스피닐기, C 6~C 60의 디아릴포스피닐기, C 6~C 60의 아릴아민기, C 5~C 60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택되며;R 1 To R 4 Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 of Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Monoaryl phosphinyl group, C 6 ~ C 60 Diaryl phosphinyl group, C 6 ~ C 60 Arylamine group, C 5 ~ C 60 It is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms;상기 L의 아릴렌기, 헤테로아릴렌기와; Ar 1 내지 Ar 2, 및 R 1 내지 R 4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C 1~C 40의 알킬기, C 2~C 40의 알케닐기, C 2~C 40의 알키닐기, C 3~C 40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C 6~C 60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C 1~C 40의 알킬옥시기, C 6~C 60의 아릴옥시기, C 1~C 40의 알킬실릴기, C 6~C 60의 아릴실릴기, C 1~C 40의 알킬보론기, C 6~C 60의 아릴보론기, C 6~C 60의 아릴포스핀기, C 6~C 60의 아릴포스핀옥사이드기, C 6~C 60의 아릴아민기, C 5~C 60의 아릴헤테로아릴아민기, 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. an arylene group and a heteroarylene group of L; Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 Heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 groups of an alkyl boron, C 6 ~ aryl boronic of C 60, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, C 6 ~ C 60 aryl amine group, C 5 ~ C 60 may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when the substituents are plural, they may be the same or different from each other can - 제1항에 있어서, According to claim 1,상기 A는 하기 구조식 중에서 선택되는 어느 하나인 화합물.Wherein A is any one selected from the following structural formula.
상기 식에서, In the above formula,*는 상기 화학식 1과 결합되는 부분을 의미한다. * means a moiety combined with Formula 1 above. - 제1항에 있어서, According to claim 1,상기 L은 단일결합이거나, 또는 하기 화학식 2로 표시되는 화합물:Wherein L is a single bond, or a compound represented by the following formula 2:[화학식 2] [Formula 2]
상기 화학식 2에서,In Formula 2,*는 상기 화학식 1과 결합이 이루어지는 부분을 의미하며, * means a portion in which a bond is formed with Chemical Formula 1,n은 1 내지 2의 정수이다. n is an integer of 1 to 2. - 제1항에 있어서, According to claim 1,상기 L은 단일결합 또는 하기 구조식 중에서 선택되는 링커인 화합물.wherein L is a single bond or a linker selected from the following structural formulae.
상기 식에서,In the above formula,*는 상기 화학식 1과 결합이 이루어지는 부분을 의미한다. * denotes a portion where a bond with Chemical Formula 1 is formed. - 제1항에 있어서, According to claim 1,Z 1 내지 Z 3는 2 ~ 3개의 N을 포함하는 화합물. Z 1 to Z 3 is a compound comprising 2 to 3 N.
- 제1항에 있어서, According to claim 1,상기 Z 1 내지 Z 3 함유 환은 하기 A-1 내지 A-3로 표시되는 치환체 군에서 선택되는 화합물:The Z 1 to Z 3 containing ring is a compound selected from the group of substituents represented by the following A-1 to A-3:
상기 A-1 내지 A-3에서, In A-1 to A-3 above,*는 상기 화학식 1과 결합이 이루어지는 부분을 의미하며, * means a portion in which a bond is formed with Chemical Formula 1,R 1, Ar 1 및 Ar 2는 각각 제1항에서 정의된 바와 같다. R 1 , Ar 1 and Ar 2 are each as defined in claim 1 . - 제1항에 있어서, According to claim 1,Ar 1 및 Ar 2는 각각 독립적으로 C 6~C 60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택되고, Ar 1 and Ar 2 are each independently selected from the group consisting of a C 6 ~ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms,상기 Ar 1 내지 Ar 2의 아릴기 및 헤테로아릴기는, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C 1~C 40의 알킬기, C 2~C 40의 알케닐기, C 2~C 40의 알키닐기, C 3~C 40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C 6~C 60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C 1~C 40의 알킬옥시기, C 6~C 60의 아릴옥시기, C 1~C 40의 알킬실릴기, C 6~C 60의 아릴실릴기, C 1~C 40의 알킬보론기, C 6~C 60의 아릴보론기, C 6~C 60의 아릴포스핀기, C 6~C 60의 아릴포스핀옥사이드기 및 C 6~C 60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. The Ar 1 To Ar 2 Aryl group and heteroaryl group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 - an aryl boronic of C 60, C 6 ~ C 60 aryl phosphine group, C 6 ~ C aryl phosphine oxide 60 group and a C 6 ~ C 60 aryl optionally substituted with 1 substituent at least one selected from the group consisting of amine groups of In this case, when the substituents are plural, they may be the same as or different from each other.
- 제1항에 있어서, According to claim 1,Ar 1 및 Ar 2는 서로 상이한 것인 화합물Ar 1 And Ar 2 A compound that is different from each other
- 제1항에 있어서, According to claim 1,R 1 내지 R 4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C 1~C 40의 알킬기, C 6~C 60의 아릴기, 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택되며,R 1 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, and 5 to 60 nuclear atoms It is selected from the group consisting of a heteroaryl group,상기 R 1 내지 R 4의 알킬기, 아릴기 및 헤테로아릴기는, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C 1~C 40의 알킬기, C 2~C 40의 알케닐기, C 2~C 40의 알키닐기, C 3~C 40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C 6~C 60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C 1~C 40의 알킬옥시기, C 6~C 60의 아릴옥시기, C 1~C 40의 알킬실릴기, C 6~C 60의 아릴실릴기, C 1~C 40의 알킬보론기, C 6~C 60의 아릴보론기, C 6~C 60의 아릴포스핀기, C 6~C 60의 아릴포스핀옥사이드기 및 C 6~C 60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. The alkyl group, aryl group and heteroaryl group of R 1 to R 4 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group , C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, arylboronic group of C 6 ~ C 60, C 6 ~ C 60 of the aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and one substituent at least one selected from the group consisting of an aryl amine of the C 6 ~ C 60 of may be substituted, and in this case, when the substituents are plural, they may be the same as or different from each other.
- 제1항에 있어서, According to claim 1,상기 화학식 1의 화합물은 하기 화학식 3 또는 4 중 어느 하나로 표시되는 화합물:The compound of Formula 1 is a compound represented by any one of the following Formulas 3 or 4:[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 3 또는 4에서, In Formula 3 or 4,Z 1~Z 3, X, Ar 1~Ar 2, L 및 n은 각각 제1항에서 정의된 바와 같다. Z 1 ~Z 3 , X, Ar 1 ~Ar 2 , L and n are each as defined in claim 1 . - 제10항에 있어서, 11. The method of claim 10,상기 화학식 3의 화합물은 하기 화학식 5 내지 화학식 8 중 어느 하나로 표시되는 화합물:The compound of Formula 3 is a compound represented by any one of Formulas 5 to 8:[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
상기 화학식 5 내지 8에서, In Formulas 5 to 8,Z 1~Z 3, X, Ar 1~Ar 2, L 및 n은 각각 제10항에서 정의된 바와 같다. Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in claim 10 . - 제10항에 있어서, 11. The method of claim 10,상기 화학식 4의 화합물은 하기 화학식 9 내지 화학식 12 중 어느 하나로 표시되는 화합물:The compound of Formula 4 is a compound represented by any one of Formulas 9 to 12:[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
상기 화학식 9 내지 12에서, In Formulas 9 to 12,Z 1~Z 3, X, Ar 1~Ar 2, L 및 n은 각각 제10항에서 정의된 바와 같다. Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in claim 10 . - 제10항에 있어서, 11. The method of claim 10,상기 화학식 3의 화합물은 하기 화학식으로 표시되는 화합물 군 중에서 선택되는 화합물.The compound of formula 3 is a compound selected from the group of compounds represented by the following formula.
- 제10항에 있어서, 11. The method of claim 10,상기 화학식 4의 화합물은 하기 화학식으로 표시되는 화합물 군 중에서 선택되는 화합물.The compound of formula 4 is a compound selected from the group of compounds represented by the following formula.
- 제1항에 있어서, According to claim 1,상기 화학식 1로 표시되는 화합물은 발광층, 전자수송층 또는 전자수송 보조층 재료인 화합물.The compound represented by Formula 1 is a material of a light emitting layer, an electron transport layer or an electron transport auxiliary layer.
- 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제15항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.A positive electrode, a negative electrode, and one or more organic material layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic material layers is an organic material comprising the compound according to any one of claims 1 to 15. electroluminescent device.
- 제16항에 있어서, 17. The method of claim 16,상기 화합물을 포함하는 유기물층은 발광층, 발광보조층, 정공주입층, 정공수송층, 전자주입층, 전자수송층, 및 전자수송 보조층으로 구성된 군에서 선택되는 유기 전계 발광 소자.The organic layer containing the compound is an organic electroluminescent device selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer.
- 제16항에 있어서, 17. The method of claim 16,상기 화합물은 발광층의 인광 호스트 재료, 전자수송층 및 전자수송 보조층 중 적어도 하나의 재료로 포함되는 유기 전계 발광 소자. The compound is an organic electroluminescent device comprising at least one of a phosphorescent host material of the light emitting layer, an electron transport layer, and an electron transport auxiliary layer.
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| KR20230081764A (en) * | 2021-11-29 | 2023-06-08 | 엘티소재주식회사 | Heterocyclic compound, organic light emitting device comprising same and composition for formation of organic material layer |
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