CN108473517A - Compounds and organic luminescent device comprising it - Google Patents
Compounds and organic luminescent device comprising it Download PDFInfo
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- CN108473517A CN108473517A CN201680077476.2A CN201680077476A CN108473517A CN 108473517 A CN108473517 A CN 108473517A CN 201680077476 A CN201680077476 A CN 201680077476A CN 108473517 A CN108473517 A CN 108473517A
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- carbon atom
- atom number
- substituted
- unsubstituted
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims description 37
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 21
- 230000005540 biological transmission Effects 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 170
- 150000001721 carbon Chemical group 0.000 claims description 163
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 238000006467 substitution reaction Methods 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- -1 substituted aryl monosilane Chemical compound 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 12
- 230000004888 barrier function Effects 0.000 claims description 11
- 150000001491 aromatic compounds Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000000707 boryl group Chemical group B* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005104 aryl silyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 150000003643 triphenylenes Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 89
- 239000000463 material Substances 0.000 description 32
- 239000002585 base Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000005416 organic matter Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 150000002220 fluorenes Chemical class 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GKEUODMJRFDLJY-UHFFFAOYSA-N 1-Methylfluorene Chemical class C12=CC=CC=C2CC2=C1C=CC=C2C GKEUODMJRFDLJY-UHFFFAOYSA-N 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- MONCAVKCQUMBQC-UHFFFAOYSA-N BrC1=CC=CC=2C3=CC=C(C=C3C(C12)(C)C)C1=CC=CC=C1 Chemical class BrC1=CC=CC=2C3=CC=C(C=C3C(C12)(C)C)C1=CC=CC=C1 MONCAVKCQUMBQC-UHFFFAOYSA-N 0.000 description 2
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- 229940125878 compound 36 Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical compound ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical class OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- MNKJQJJUQKPGDJ-UHFFFAOYSA-N 1,2-dibromo-9,9-dimethylfluorene Chemical class C1=C(Br)C(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 MNKJQJJUQKPGDJ-UHFFFAOYSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical class C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000005024 alkenyl aryl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical group [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to novel organic compound and include its Organic Light Emitting Diode.The organic luminescent device for including organic compound of the present invention, the transmission capacity of electronics is outstanding, and low-voltage is presented and high efficiency, electrons and holes are moved in conjunction with region, outstanding chromaticity coordinates is presented.
Description
Technical field
The present invention relates to novel organic compound and include its organic luminescent device.
Background technology
In Organic Light Emitting Diode (organic luminescent device or organic electroluminescence device), it is used as the material of organic matter layer
Can be broadly dassified into according to function emitting layer material, hole injection layer material, hole transport layer material, electron transport layer material,
Electron injecting layer material, hole barrier layer material etc..Also, above-mentioned luminescent material can be macromolecule and list according to molecular weight
Molecule can be classified as the fluorescent material of the singlet excited state from electronics and from the triple of electronics according to luminescence mechanism
Delayed fluorescence material of the movement of the phosphor material and electronics of state excited state from triplet excitation state to singlet excited state.
Luminescent material can be classified as blue, green, red illuminating material according to illuminant colour and embody better natural colour institute
The yellow and orange light emitting materials needed.Also, in order to increase excitation purity, and luminous efficiency is increased by energy transfer, it can be by master
Body/dopant class is used as luminescent substance.If its principle is by compared with the main body of main composition luminescent layer, band gap is small and luminous
The outstanding dopant of efficiency is mixed in auxiliary layer on a small quantity, then the exciton generated in main body is conveyed to dopant, to send out
Efficient light.At this point, the wavelength of main body is moved to the wavelength band of dopant, thus can be according to the dopant and main body utilized
Type obtains the light of required wavelength.
So far, as the substance for being used in this organic luminescent device, well-known there are many compounds, but are utilizing
So far in the case of the organic luminescent device of well-known substance, due to high driving voltage, low efficiency and short life, because
And it is difficult to functionization.Therefore, ongoing effort is developed using the substance with outstanding characteristic with low voltage drive, high brightness
And the organic luminescent device of long-life.
The organic compound comprising phosphine oxide and fluorenes is disclosed in Korean Patent Publication KR 10-1027582, still,
Fluorenes forms spirane structure, is taken off in Korean Patent Laid KR 10-2013-0129543 and KR 10-2014-0100910
Show the organic compound comprising phosphine oxide and fluorenes, but as above-mentioned, fluorenes forms spirane structure, not specifically disclosed by above compound
Organic luminescent device as electron-transferring material.
Compound comprising phosphine oxide is used in electron transfer layer, hole blocking layer or the two by the present invention, to increase
The mobility for powering up son provides stability, and realize high efficiency thus when preparing organic luminescent device to film.
Invention content
The object of the present invention is to provide can prepare that outstanding chromaticity coordinates is presented, and having with high efficiency and long-life
The organic compound of machine luminescent device.
By the result of study of the above problem, the inventors discovered that being realized by the organic compound that following formula 1 indicates
Thus above-mentioned purpose completes the present invention.
Chemical formula 1
In above-mentioned chemical formula 1,
A and B is each independently hydrogen, halogen, cyano, the alkyl that substituted or unsubstituted carbon atom number is 1 to 30, substitution
Or unsubstituted carbon atom number be 6 to 30 aryl, substituted or unsubstituted carbon atom number be 3 to 30 heteroaryl, substitution or
Unsubstituted (aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30), substituted or unsubstituted carbon
Alkoxy that naphthenic base that atomicity is 3 to 30, substituted or unsubstituted carbon atom number are 1 to 30, substituted or unsubstituted carbon
Arylsilyl that alkylsilyl groups that atomicity is 1 to 30, substituted or unsubstituted carbon atom number are 6 to 30, substitution or not
(aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30) monosilane of substitution, substitution or unsubstituted
Carbon atom number be 1 to 30 alkyl amino, substituted or unsubstituted carbon atom be 6 to 30 arylamino or substitution or
At least one of unsubstituted (alkyl that carbon atom is 1 to 30) (aryl that carbon atom number is 6 to 30) amino, A and B be
X and Y are each independently CR1Or N；
R0It is each independently hydrogen, the alkyl that substituted or unsubstituted carbon atom number is 1 to 30, substituted or unsubstituted carbon
The heteroaryl that the aryl or substituted or unsubstituted carbon atom that atomicity is 6 to 30 are 3 to 30, but, adjacent R0It is connected
And condensed ring is formed, without forming spirane structure；
R1Be each independently hydrogen, heavy hydrogen, halogen, cyano, substituted or unsubstituted carbon atom number be 1 to 30 alkyl,
Heteroaryl that aryl that substituted or unsubstituted carbon atom number is 6 to 30, substituted or unsubstituted carbon atom number are 3 to 30 takes
Generation or unsubstituted (aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30), substitution or unsubstituted
Carbon atom number be 3 to 30 naphthenic base, substituted or unsubstituted carbon atom number be 1 to 30 alkoxy, substitution or unsubstituted
Carbon atom number be 1 to 30 alkylsilyl groups, substituted or unsubstituted carbon atom number be 6 to 30 arylsilyl, substitution
Or it unsubstituted (aromatic compound that carbon atom is 6 to 30) (alkyl that carbon atom number is 1 to 30) monosilane, substitution or does not take
The arylamino or substitution that alkyl amino that the carbon atom number in generation is 1 to 30, substituted or unsubstituted carbon atom are 6 to 30
Or unsubstituted (alkyl that carbon atom is 1 to 30) (aryl that carbon atom number is 6 to 30) amino；
Above-mentioned heteroaryl includes more than one hetero atom in B, N, O, S, Si and P.
Organic luminescent device is prepared using the organic compound of the present invention, there is electronics to attract by oxide special
Property, thus the transmission capacity of electronics is outstanding, is presented low-voltage and high efficiency, and electronics and hole are moved in conjunction with region,
Outstanding chromaticity coordinates is presented.
Description of the drawings
Fig. 1 shows the structures of the organic luminescent device of one embodiment of the present invention.
Specific implementation mode
Hereinafter, the present invention is described in more detail, but this is not construed as limiting the scope of the present invention for illustrating
Method.
Further illustrate the compound indicated by above-mentioned chemical formula 1 as follows.
Recorded " alkyl that carbon atom number is 1 to 30 " means that form the carbon atom number of chain is 1 to 30 in the present invention
Linear or branched alkyl group, wherein can be carbon atom number be 1 to 10 specifically, more specifically, can be 1 to 6.Make
For the concrete example of abovementioned alkyl, there are methyl, ethyl, n- propyl, isopropyl, n- butyl, isobutyl group and tert-butyl etc..In this hair
In bright, " alkenyl that carbon atom number is 2 to 30 " means to form the linear chain or branched chain alkenyl that the carbon atom number of chain is 2 to 30,
In, can be specifically carbon atom number it be 2 to 20, more specifically, can be 2 to 10.As the concrete example of above-mentioned alkenyl,
There are vinyl, 1- propyl phenyls, 2- propyl phenyls, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 2- methyl but-2-ene bases etc..At this
In invention, " alkynyl that carbon atom number is 2 to 30 " means to form the linear chain or branched chain alkynyl that the carbon atom number of chain is 2 to 30,
Wherein, specifically, can be carbon atom number it be 2 to 20, more specifically, can be 2 to 10.As the example of above-mentioned alkynyl,
There are amyl- 2- alkynyls of acetenyl, 1- propinyls, 2-propynyl, 1- butynyls, 2- butynyls, 3- butynyls, 1- methyl etc..At this
In invention, " naphthenic base that carbon atom number is 3 to 30 " means the monocycle or polycyclic hydrocarbon that ring skeleton carbon atom number is 3 to 30,
Wherein, specifically, can be carbon atom number it be 3 to 20, more specifically, can be 3 to 7.As the example of above-mentioned naphthenic base,
There are cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc..In the present invention, " Heterocyclylalkyl that carbon atom number is 3 to 7 " means ring
Backbone carbon atoms number is 3 to 7, including the more than one hetero atom in the group being made of B, N, O, S, Si and P, specifically
Ground, including selected from O, S and N more than one heteroatomic naphthenic base, for example, have tetrahydrofuran, pyrrolidines, thiophane,
Oxinane etc..In the present invention, " (Asia) aryl that carbon atom number is 6 to 30 " mean be from ring skeleton carbon atom number
The monocycle or condensed ring system group of 6 to 30 aromatic hydrocarbon, wherein can be ring skeleton carbon atom number be 6 to 20 specifically, more
Specifically, it can be 6 to 15.As the example of above-mentioned aryl, there are phenyl, xenyl, terphenyl, naphthalene, binaphthyl, phenyl
Naphthalene, naphthylphenyl, fluorenyl, phenylfluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, phenyl phenanthryl, anthryl, indenyl, Sanya
Phenyl, pyrenyl, aphthacene base, base,Base, benzanthracene, fluoranthene base etc..In the present invention, " carbon atom number be 3 to 30 it is miscellaneous
(Asia) aryl " means that ring skeleton carbon atom number is 3 to 30, including one in the group being made of B, N, O, S, Si and P
A above heteroatomic aryl.Hetero atom number specifically can be 1 to 4, can be monocycle system or with it is more than one
Condensed ring system made of phenyl ring condensation, can be with fractional saturation.Also, in the present invention, above-mentioned heteroarylene also includes one
The form that the above heteroaryl or aryl are connected by singly-bound with heteroaryl.As the example of above-mentioned heteroaryl, there are furyl, benzene sulphur
Base, pyrrole radicals, imidazole radicals, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyls, three
Monocycles system heteroaryl, the benzene such as piperazine base, tetrazine base, triazolyl, tetrazole radical, furan cluck base, pyridyl group, pyrazinyl, pyrimidine radicals, pyridazinyl
And furyl, aisaa benzothiophenyl, isobenzofuran-base, dibenzofuran group, dibenzo thiophenyl, benzo naphthalene thiophenyl, benzo
Imidazole radicals, benzothiazolyl, benzisothia oxazolyl, benzoxazine, benzoxazolyl, isoindolyl, indyl, indazole
Base, diazosulfide base, quinolyl, isoquinolyl, cinnoline base, quinazolyl, quinoxalinyl, carbazyl, phenoxazine groups, phenanthridines
Condensed ring systems heteroaryl such as base, benzodioxole etc..In the present invention, " halogen " includes F, Cl, Br and I atom.
In the present invention, the compound indicated by above-mentioned chemical formula 1 can be indicated by following formula 2 or 3.
Chemical formula 2
Chemical formula 3
In above-mentioned chemical formula 2 and 3, X, Y and R0It is identical as the definition in chemical formula 1.
Also, " substitution " means in certain functions in the contents of recorded " substitution is unsubstituted " in the present invention
Hydrogen atom is replaced by other atoms or other functional groups's (base replaces body) in group.In above-mentioned A, B, R of above-mentioned chemical formula 10And
R1In, substitution alkyl, substituted alkoxy, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substitution alkylsilyl groups, substitution virtue
Base monosilane, substituted aralkyl monosilane, substituted aryl amino, substitution alkyl amino, substitution alkyl aryl amino and substitution virtue
The substitution body of alkyl mean each independently selected from by heavy hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, carbon atom number be 1 to
Alkenyl that 30 alkyl, halogen (alkyl that carbon atom number is 1 to 30), carbon atom number are 2 to 30, carbon atom number are 2 to 30
The cycloalkanes that alkyl sulfenyl that alkoxy that alkynyl, carbon atom number are 1 to 30, carbon atom number are 1 to 30, carbon atom number are 3 to 30
Aryloxy group that Heterocyclylalkyl that cycloalkenyl group that base, carbon atom number are 3 to 30, carbon atom number are 3 to 7, carbon atom number are 6 to 30,
Arylthio that carbon atom number is 6 to 30, the substituted or unsubstituted carbon atom number of aryl for being 6 to 30 by carbon atom number are 3 to 30
Heteroaryl, carbon atom number be 3 to 30 the substituted or unsubstituted carbon atom number of heteroaryl be 6 to 30 aryl, three (carbon atoms
The alkyl that number is 1 to 30) monosilane, three (aryl that carbon atom number is 6 to 30) monosilanes, the two (alkane that carbon atom number is 1 to 30
Base) (aryl that carbon atom number is 6 to 30) monosilane, (alkyl that carbon atom number is 1 to 30) two (carbon atom number is 6 to 30
Aryl) monosilane, amino, mono- or two-carbon atom numbers be 1 to 30 alkyl amino, mono- or two-carbon atom numbers be 6 to 30
Arylamino, (alkyl that carbon atom number is 1 to 30) (aryl that carbon atom number is 6 to 30) amino, carbon atom number are 1 to 30
Aryl carbonyl that alkoxy carbonyl that alkyl-carbonyl, carbon atom number are 1 to 30, carbon atom number are 6 to 30, two (carbon atom numbers 6
Aryl to 30) boryl, two (alkyl that carbon atom number is 1 to 30) boryls, (alkyl that carbon atom number is 1 to 30) (carbon atom
The aryl that number is 6 to 30) boryl, (aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30) and
(alkyl that carbon atom number is 1 to 30) (aryl that carbon atom number is 6 to 30) composition group in more than one, specifically can be each
From independently be the aryl for being 6 to 30 by cyano, carbon atom number and by carbon atom number be 6 to 12 aryl it is substituted or unsubstituted
Carbon atom number is more than one in the group of 3 to 15 heteroaryl composition.
In above-mentioned chemical formula 1, A and B can be specifically each independentlyOrIn A and B
It is at least one to be
X and Y can specifically be each independently CR1。
R0Alkyl or the substitution or not that substituted or unsubstituted carbon atom number is 1 to 6 can be specifically each independently
The aryl that substituted carbon atom number is 6 to 12, it is highly preferred that methyl or phenyl can be each independently.
R1The aryl or substitution of hydrogen, substituted or unsubstituted carbon atom number for 6 to 30 can be specifically each independently
Or the heteroaryl that unsubstituted carbon atom number is 3 to 30.More specifically it is each independently substituted or unsubstituted phenyl, substitution
Or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted Sanya
Phenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical or substitution
Or unsubstituted benzimidazolyl, substituent group at this time can be cyano, phenyl, by the triazine radical of phenyl substitution or by phenyl
Substituted benzimidazolyl.
Other embodiments according to the present invention, in above-mentioned chemical formula 1, A and B are each independentlyOrAt least one of A and B areX and Y are each independently CR1；R0Each independently
For substituted or unsubstituted carbon atom number be 1 to 6 alkyl or substituted or unsubstituted carbon atom number be 6 to 12 aryl；
R1It is each independently the aryl or substituted or unsubstituted carbon atom of hydrogen, substituted or unsubstituted carbon atom number for 6 to 30
The heteroaryl that number is 3 to 30.
Other embodiments according to the present invention, in above-mentioned chemical formula 1, A and B are each independentlyOrAt least one of A and B areX and Y are each independently CR1；R0Each independently
For methyl or phenyl；R1It is each independently substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substitution or does not take
The terphenyl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl group,
Substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical or substituted or unsubstituted benzimidazolyl, at this time
Substituent group is cyano, phenyl, the triazine radical replaced by phenyl or the benzimidazolyl replaced by phenyl.
The compound indicated by above-mentioned chemical formula 1 can more specifically be illustrated as following compound, but not limited to this.
The organic compound of the present invention can be prepared according to synthetic method well known to those skilled in the art.
The present invention provide comprising chemical formula 1 compound electron-transferring material or hole barrier materials and include electronics pass
Pass the organic luminescent device of material or hole barrier materials.Above-mentioned electron-transferring material or hole barrier materials are by chemical formula 1
Compound independently forms, or can also be additional comprising conventional included in electron-transferring material or hole barrier materials
The electron transfer layer use or hole blocking layer mixture or composition of substance.
The present invention organic luminescent device include：Anode；Cathode；And 1 layer between the above-mentioned anode of intervention and cathode with
On organic matter layer, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer can contain main body and dopant.Above-mentioned luminescent layer is
The luminous layer of fingering row, can be single layer, furthermore it is possible to be multiple layers made of the layer laminate by 2 or more.For above-mentioned hair
The doping concentration of the dopant compound of the host compound of photosphere is less than 20 weight percent, this in terms of the efficiency of device on
Seem outstanding.
Also, the organic luminescent device of the present invention, may include electron-transferring material, as luminescent layer in above-mentioned organic matter layer
Dopant reproducibility dopant can be used.Above-mentioned reproducibility dopant can select free alkali metal, alkaline-earth metal, terres rares
Metal, the oxide of alkali metal, the halide of alkali metal, the oxide of alkaline-earth metal, the halide of alkaline-earth metal, rare earth eka-gold
The organic complex and terres rares of the oxide of category, the halide of rare earth metal, the organic complex of alkali metal, alkaline-earth metal
One or more of the group of the organic complex composition of metal.
The organic luminescent device of the present invention can also be added in organic matter layer comprising selected from by aryl amine compound and benzene second
More than one compound in the group of alkenyl aryl aminated compounds composition.
Also, with regard to the present invention organic luminescent device for, organic matter layer can also add comprising selected from 1 race, 2 races, 4 weeks
Phase transition metal, 5 row transition metals, lanthanide series metal and d- transition elements organic metal composition group in more than one gold
Category or more than one complex compound comprising these metals.
For the organic luminescent device of the present invention, the inner surface in at least side of a pair of electrodes is configurable selected from sulphur
More than one layer in race's compound (chalcogenide) layer, halogenated metal layer and metal oxide layer is (hereinafter, these are claimed
Be " superficial layer ").Specifically, the chalkogenide of silicon and aluminium is can configure (comprising oxidation in the anode surface of luminescence medium layer side
Object) layer, and can configure halogenated metal layer or metal oxide layer in the cathode surface of luminescence medium layer side.According to above-mentioned superficial layer
The driving that can get organic luminescent device stabilizes.As the concrete example of above-mentioned chalkogenide, there is SiOX(1≤X≤2)、AlOX(1
≤ X≤1.5), SiON or SiAlON etc., as the concrete example of metal halide, there is LiF, MgF2、CaF2, rare earth fluoride metalloid
Deng as the concrete example of metal oxide, there is Cs2O、Li2O, MgO, SrO, BaO, CaO etc..
Hole injection layer, hole transport layer or electronic barrier layer or their group can be used between anode and luminescent layer
It closes.Hole injection layer for the hole injection barrier reduced from anode to hole transport layer or electronic barrier layer, (or note by hole
Enter voltage) purpose, multiple layers, each layer can be used to can be used simultaneously 2 compounds.Hole transport layer or electronic barrier layer also may be used
Use multiple layers.
Electron buffer layer, hole blocking layer, electron transfer layer or electron injecting layer can be used between luminescent layer and cathode
Or combination thereof.Electron buffer layer is for adjusting electron injection and improve the interfacial characteristics between luminescent layer and electron injecting layer
Purpose, multiple layers, each layer can be used to can be used simultaneously 2 compounds.Hole blocking layer or electron transfer layer can also be used more
Multiple compounds can be used in a layer, each layer.
Above-mentioned hole injection layer, hole transport layer, electronic barrier layer, electron buffer layer, hole blocking layer, electron transfer layer
And material included in electron injecting layer, as long as well known material, using even which kind of.
Also, for the organic luminescent device of the present invention, electricity can also configure in an at least side surface for a pair of electrode
Son transmits compound and the Mixed Zone of reproducibility dopant or the Mixed Zone of hole transport compounds and oxidisability dopant.
Since according to this mode, electron transport compound is reduced to anion, therefore is readily injected into from Mixed Zone to luminescence medium
And transmit electronics.Also, since hole transport compounds are by oxidation and as cation, from Mixed Zone to luminescence medium
It is readily injected into and transmits hole.As oxidisability dopant, various lewis acids and electronics can be enumerated to acceptor
(acceptor) compound can enumerate alkali metal, alkali metal compound, alkaline-earth metal, rare earth eka-gold as reproducibility dopant
Category and their mixture.Also, reproducibility dopant layer is used as charge generating layers, can be prepared with more than two luminescent layers
The white luminous organic luminescent device of progress.
The dry types such as the applicable vacuum deposition of formation of each layer of the organic luminescent device of the present invention, sputtering, plasma coating
Any one of the wet type membrane formations such as membrane formation process or spin coating, dip-coating (dip coating), flow coat method.
For wet type membrane formation, the material for forming each layer is dissolved or dispersed in ethyl alcohol, chloroform, tetrahydrofuran, bis- Evil
In the solvent appropriate such as alkane, chlorobenzene, dichloro-benzenes, methoxybenzene, film is formed, can dissolve in the solvent or dispersion forms each layer
Material, as long as not being a problem to film forming, even which kind of is selected.
Hereinafter, in order to which the present invention is understood in detail, the representation compound of the present invention is enumerated, to illustrate the organic compound of the present invention
The characteristics of luminescence of object and preparation method thereof and organic luminescent device comprising the organic compound.
The synthesis of [embodiment 1] compound 1
Under argon or nitrogen atmosphere, in 250mL flasks, bromo- 9, the 9- dimethyl fluorenes (54.6g, 200mmol) of 2- are dissolved in four
Hydrogen furans (THF) 500mL.At -78 DEG C, wherein being put into n-BuLi (2.5M) 88mL.After being maintained 1 hour at -78 DEG C, put
Enter dichloro phosphine 13.5mL, stirs 12 hours at normal temperatures.If reaction no longer carries out, it is put into distilled water 200mL, uses dichloromethane
(MC) 30mL is extracted 3 times.After removing moisture removal with anhydrous sodium sulfate, solvent is removed, obtains solid.The solid of acquisition is dissolved in MC
In 200mL, H is put at 0 DEG C2O220mL.After being reacted 3 hours at 0 DEG C, extracted 3 times with MC 20mL.Use anhydrous slufuric acid
Sodium is gone after moisture removal, by hexane:Ethyl acetate (1:1) it is used as mobile phase to carry out post separation, obtains compound as white solid 1
(36g, 60%).
MS calculated values：510.60；MS measured values：510.21[M].
The synthesis of [embodiment 2] compound 2
The synthesis of the bromo- 7- phenyl -9,9- dimethyl fluorenes of 2-
Under argon or nitrogen atmosphere, in 250mL flasks, it is put into 2,7-, bis- bromo- 9,9- dimethyl fluorenes 35g, phenylboric acid
15g, tetrakis triphenylphosphine palladium (0) 2.5g, dioxanes 300mL and sodium carbonate 35g are dissolved in solution made of water 100mL, reflux, and 24
Hour heating stirring.After reaction, the crystallization being precipitated to being cooled to room temperature is filtered separation.It is recrystallized with toluene
Change, obtains bromo- 7- phenyl -9, the 9- dimethyl fluorenes of white solid 2- (24.5g, 70%).
The synthesis of compound 2
Under argon or nitrogen atmosphere, in 250mL flasks, by bromo- 7- phenyl -9, the 9- dimethyl fluorenes of 2- (54.5g,
200mmol) it is dissolved in THF 500mL.At -78 DEG C, wherein being put into n-BuLi (2.5M) 88mL.Maintained at -78 DEG C 1 hour it
Afterwards, it is put into dichloro phosphine 13.5mL, is stirred 12 hours at normal temperatures.If reaction no longer carries out, it is put into distilled water 200mL, uses MC
30mL is extracted 3 times.After removing moisture removal with anhydrous sodium sulfate, solvent is removed, obtains solid.The solid of acquisition is dissolved in MC
In 200mL, H2O2 20mL are put at 0 DEG C.After being reacted 3 hours at 0 DEG C, extracted 3 times with MC 20mL.Use anhydrous slufuric acid
Sodium is gone after moisture removal, by hexane:Ethyl acetate (1:1) it is used as mobile phase to carry out post separation, obtains compound as white solid 2
(36.4g, 63%).
MS calculated values：662.80；MS measured values：662.27[M].
The synthesis of [embodiment 3] compound 12
In embodiment 1, bromo- 9, the 9- dimethyl fluorenes of 2- are replaced using bromo- 9, the 9- diphenylfluorenes of 2-, in addition to this, led to
Identical method synthesis is crossed, compound as white solid 12 (34g, 58%) is obtained.
MS calculated values：758.88；MS measured values：758.27[M].
The synthesis of [embodiment 4] compound 4
The synthesis of the bromo- 7- of 2- (3- pyridines) -9,9- dimethyl fluorenes
In example 2, phenylboric acid is replaced using 3- pyridine boronic acids, in addition to this, is synthesized by identical method,
Obtain the bromo- 7- of 2- (3- pyridines) -9,9- dimethyl fluorenes (22g, 65%).
The synthesis of compound 4
In example 2, the bromo- 7- phenyl -9,9- of 2- bis- is replaced using the bromo- 7- of 2- (3- pyridines) -9,9- dimethyl fluorenes
In addition to this methyl fluorenes is synthesized by identical method, obtain compound as white solid 4 (33.2g, 59%).
MS calculated values：664.77；MS measured values：664.26[M].
The synthesis of [embodiment 5] compound 23
Under argon or nitrogen atmosphere, in 500mL flasks, it is put into bromo- 9, the 9- dimethyl fluorenes 27.3g of 2-, diphenyl phosphine oxide
30g, anhydrous phosphoric acid potassium 41g, dichloro (1,3- (double diphenylphosphinos) propylene) nickel (II) 3.25g are Ji dioxane 250mL, reflux,
24 hours heating stirrings.If reaction no longer carries out, it is cooled to room temperature, distilled water 200mL is added, is extracted 3 times with MC 30mL.
After removing moisture removal with anhydrous sodium sulfate, by hexane:Ethyl acetate (1:1) it is used as mobile phase to carry out post separation, it is solid to obtain white
Body compound 23 (20g, 50%).
MS calculated values：394.44；MS measured values：394.15[M].
The synthesis of [embodiment 6] compound 24
The synthesis of the bromo- 7- phenyl -9,9- dimethyl fluorenes of 2-
Under argon or nitrogen atmosphere, in 250mL flasks, it is put into 2,7- dibromos- 9,9- dimethyl fluorenes 35g, phenylboric acid
15g, tetrakis triphenylphosphine palladium (0) 2.5g, dioxanes 300mL and sodium carbonate 35g are dissolved in solution made of water 100mL, reflux, and 24
Hour heating stirring.After reaction, the crystallization being precipitated to being cooled to room temperature is filtered separation.It is recrystallized with toluene
Change, obtains bromo- 7- phenyl -9, the 9- dimethyl fluorenes of white solid 2- (24.5g, 70%).
The synthesis of compound 24
Under argon or nitrogen atmosphere, in 500mL flasks, it is put into bromo- 7- phenyl -9, the 9- dimethyl fluorene 27.4g of 2-, diphenyl
Phosphine oxide 30g, anhydrous phosphoric acid potassium 41g, dichloro (1,3- (double diphenylphosphinos) propylene) nickel (II) 3.25g Ji dioxane 250mL,
Reflux, 24 hours heating stirrings.If reaction no longer carries out, it is cooled to room temperature, distilled water 200mL is added, is extracted with MC 30mL
3 times.After removing moisture removal with anhydrous sodium sulfate, by hexane:Ethyl acetate (1:1) it is used as mobile phase to carry out post separation, obtains white
Color solid chemical compound 24 (19.4g, 49%).
MS calculated values：470.54；MS measured values：470.18[M].
The synthesis of [embodiment 7] compound 36
The synthesis of the bromo- 7- of 2- (2- xenyls) -9,9- dimethyl fluorenes
In embodiment 6, phenylboric acid is replaced using 2- biphenylboronics, in addition to this, is closed by identical method
At the acquisition bromo- 7- of 2- (2- xenyls) -9,9- dimethyl fluorenes (25g, 69%).
The synthesis of compound 36
In embodiment 6, the bromo- 7- phenyl -9,9- of 2- is replaced using the bromo- 7- of 2- (2- xenyls) -9,9- dimethyl fluorenes
In addition to this dimethyl fluorene is synthesized by identical method, obtain compound as white solid 36 (37g, 61%).
MS calculated values：546.64；MS measured values：546.21[M].
The synthesis of [embodiment 8] compound 31
The bromo- 7- of 2- (2- (3- bromophenyls) -4,6- diphenyl -1,3,5- triazines) -9,9'- dimethylThe synthesis of fluorenes
In example 2, phenylboric acid is replaced using 3- pyridine boronic acids, in addition to this, is synthesized by identical method,
Obtain the bromo- 7- of 2- (3- pyridines) -9,9- dimethyl fluorenes (22g, 65%).
The synthesis of compound 31
In example 2, the bromo- 7- phenyl -9,9- of 2- bis- is replaced using the bromo- 7- of 2- (3- pyridines) -9,9- dimethyl fluorenes
In addition to this methyl fluorenes is synthesized by identical method, obtain compound as white solid 31 (33.2g, 59%).
MS calculated values：701.79；MS measured values：701.26[M].
The preparation of organic luminescent device
Structure recorded in Fig. 1, prepares organic luminescent device.Organic luminescent device to it is lower and on stack gradually anode
14/ electron transfer layer of (hole injecting electrode 11)/hole injection layer 12/ hole transport layer, 13/ luminescent layer, 15/ cathode (note by electronics
Enter electrode 16).
In Fig. 1, substrate 10 can be that transparent glass substrate is either flexible when preparing organic luminescent device
Plastic base.
Hole injecting electrode 11 is used as the anode for hole injection of organic luminescent device.It utilizes so that hole can be injected
Mode have low work function substance, can by tin indium oxide (ITO), indium zinc oxide (IZO), graphene (graphene) it
The transparent material of class is formed.
In the hole injection layer 12 of device preparation example and comparative example, hole transport layer 13, luminescent layer 14, electron transfer layer 15
Use following substance.
The cathode 16 for injecting electronics is formed on electron injecting layer 15.As cathode, various metals can be used.As
Specific example has the substances such as aluminium, gold, silver.
[device preparation example 1] includes the preparation of the organic luminescent device of the organic compound of the present invention
The glass substrate that tin indium oxide (ITO) is applied as to film by distilled water ultrasonic wave washs.If distilled water
Washing terminates, then carries out ultrasonic washing using the solvent of isopropanol, acetone, methanol etc., and after being dried, and is transferred to
Plasma cleaner after then being cleaned aforesaid substrate 5 minutes using oxygen plasma, is utilized on tin indium oxide substrate top
Thermal vacuum depositor (thermal evaporator) will as hole injection layerHT01 be filmed, as sky
Cave transfer layer, willRef.4 be filmed.Then, as above-mentioned luminescent layer, 5% BH01 is adulterated：BD01, withIt is filmed.Then, as electron supplying layer, compound 1 and Liq are pressed 1：1 ratio withAfter film,
As electron injecting layer, by LiFIt is filmed, as cathode, by aluminium (Al)It is filmed, and should
Device is sealed (Enca psulation) in glove box, to be prepared for organic luminescent device.
[device preparation example 2 to 8] includes the preparation of the organic luminescent device of the electron-transferring material of the present invention
By method identical with device preparation example 1, manufacture is respectively using compound 2 to 8 come will be electric instead of compound 1
The organic luminescent device that sub- transfer layer is filmed.
[comparative example 1] includes the preparation of the organic luminescent device of previous electron-transferring material
As the electron transfer layer of device preparation example 1, compound 1 is replaced using ET01, in addition to this, by identical
Method prepares device.
[comparative example 2] includes the preparation of the organic luminescent device of previous electron-transferring material
As the electron transfer layer of device preparation example 1, compound 1 is replaced using ET02, in addition to this, by identical
Method prepares device.
The performance evaluation of organic luminescent device
Apply electricity using 2400 source measuring unit of Keithley (Kiethley 2400source measureme nt unit)
It presses to inject electronics and hole, is measured using Konica Minolta (Konica Minolta) spectroradiometer (CS-2000)
Thus under atmospheric conditions brightness when shining is measured for applying alive current density and brightness, to have rated reality
The performance of the organic luminescent device of example and comparative example is applied, and the results are shown in table 1.
Table 1
The chromaticity coordinates and life characteristic for confirming the device of the organic compound comprising the present invention, compared with including previous material
Device for, it is more excellent.
Claims (8)
1. a kind of organic compound, which is characterized in that indicated by following formula 1：
Chemical formula 1
In the chemical formula 1,
A and B be each independently hydrogen, halogen, cyano, substituted or unsubstituted carbon atom number be 1 to 30 alkyl, substitution or not
Heteroaryl that aryl that substituted carbon atom number is 6 to 30, substituted or unsubstituted carbon atom number are 3 to 30, substitution do not take
(aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30), the substituted or unsubstituted carbon atom in generation
Alkoxy that naphthenic base that number is 3 to 30, substituted or unsubstituted carbon atom number are 1 to 30, substituted or unsubstituted carbon atom
Arylsilyl that alkylsilyl groups that number is 1 to 30, substituted or unsubstituted carbon atom number are 6 to 30, substitution or unsubstituted
(aromatic compound that carbon atom is 6 to 30) (alkyl that carbon atom number is 1 to 30) monosilane, substituted or unsubstituted carbon it is former
Arylamino that alkyl amino that son is 1 to 30, substituted or unsubstituted carbon atom are 6 to 30 or substituted or unsubstituted
(alkyl that carbon atom is 1 to 30) (aryl that carbon atom number is 6 to 30) amino, at least one of A and B are
X and Y are each independently CR1Or N；
R0It is each independently hydrogen, the alkyl that substituted or unsubstituted carbon atom number is 1 to 30, substituted or unsubstituted carbon atom
The heteroaryl that the aryl or substituted or unsubstituted carbon atom that number is 6 to 30 are 3 to 30, but, adjacent R0It is connected and shape
At condensed ring, without forming spirane structure；
R1Be each independently hydrogen, heavy hydrogen, halogen, cyano, substituted or unsubstituted carbon atom number be 1 to 30 alkyl, substitution or
Heteroaryl that aryl that unsubstituted carbon atom number is 6 to 30, substituted or unsubstituted carbon atom number are 3 to 30, substitution or not
(aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30), the substituted or unsubstituted carbon of substitution are former
Alkoxy that naphthenic base that subnumber is 3 to 30, substituted or unsubstituted carbon atom number are 1 to 30, substituted or unsubstituted carbon are former
Arylsilyl that alkylsilyl groups that subnumber is 1 to 30, substituted or unsubstituted carbon atom number are 6 to 30, substitution do not take
(aromatic compound that carbon atom is 6 to 30) (alkyl that carbon atom number is 1 to 30) monosilane, the substituted or unsubstituted carbon in generation
Arylamino that alkyl amino that atomicity is 1 to 30, substituted or unsubstituted carbon atom are 6 to 30 or substitution do not take
(alkyl that carbon atom is 1 to 30) (aryl that carbon atom number is 6 to the 30) amino in generation；
The heteroaryl includes more than one hetero atom in B, N, O, S, Si and P.
2. organic compound according to claim 1, which is characterized in that the chemical formula 1 is by following formula 2 or 3 tables
Show：
Chemical formula 2
Chemical formula 3
In the chemical formula 2 and 3,
X, Y and R0As defined in claim 1.
3. organic compound according to claim 1, which is characterized in that in described A, B, R0And R1In, substitution alkyl takes
For alkoxy, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substitution alkylsilyl groups, substituted aryl monosilane, substitution virtue
Alkylsilyl groups, substitution alkyl amino, replace the substitution body of alkyl aryl amino and substituted aralkyl respectively at substituted aryl amino
It independently is selected from by heavy hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, the alkyl that carbon atom number is 1 to 30, halogen (carbon atom
The alkyl that number is 1 to 30), carbon atom number be 2 to 30 alkenyl, carbon atom number be 2 to 30 alkynyl, carbon atom number be 1 to 30
Alkoxy, carbon atom number be 1 to 30 alkyl sulfenyl, carbon atom number be 3 to 30 naphthenic base, carbon atom number be 3 to 30
The fragrant sulphur that aryloxy group that Heterocyclylalkyl that cycloalkenyl group, carbon atom number are 3 to 7, carbon atom number are 6 to 30, carbon atom number are 6 to 30
Heteroaryl that base, the substituted or unsubstituted carbon atom number of the aryl for being 6 to 30 by carbon atom number are 3 to 30 by carbon atom number is 3
Aryl that the substituted or unsubstituted carbon atom number of heteroaryl to 30 is 6 to 30, three (alkyl that carbon atom number is 1 to 30) first silicon
Alkane, three (aryl that carbon atom number is 6 to 30) monosilanes, (carbon atom number is 6 to 30 to two (alkyl that carbon atom number is 1 to 30)
Aryl) it is monosilane, (alkyl that carbon atom number is 1 to 30) two (aryl that carbon atom number is 6 to 30) monosilane, amino, mono-
Or two-carbon atom number be 1 to 30 alkyl amino, mono- or two-carbon atom numbers be 6 to 30 arylamino, (carbon atom number 1
Alkyl to 30) (aryl that carbon atom number is 6 to 30) amino, carbon atom number be 1 to 30 alkyl-carbonyl, carbon atom number 1
To 30 alkoxy carbonyl, the aryl carbonyl that carbon atom number is 6 to 30, two (aryl that carbon atom number is 6 to 30) boryls, two
(alkyl that carbon atom number is 1 to 30) boryl, (alkyl that carbon atom number is 1 to 30) (aryl that carbon atom number is 6 to 30) boron
Base, (aromatic compound that carbon atom number is 6 to 30) (alkyl that carbon atom number is 1 to 30) and (alkane that carbon atom number is 1 to 30
Base) (carbon atom number be 6 to 30 aryl) composition group in more than one.
4. organic compound according to claim 1, which is characterized in that A and B are each independentlyAt least one of A and B are
X and Y are each independently CR1；
R0It is each independently alkyl or the substituted or unsubstituted carbon atom that substituted or unsubstituted carbon atom number is 1 to 6
The aryl that number is 6 to 12；
R1It is each independently the aryl or substituted or unsubstituted carbon of hydrogen, substituted or unsubstituted carbon atom number for 6 to 30
The heteroaryl that atomicity is 3 to 30.
5. organic compound according to claim 1, which is characterized in that A and B are each independentlyAt least one of A and B are
X and Y are each independently CR1；
R0It is each independently methyl or phenyl；
R1It is each independently substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl
Base, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl group, substitution do not take
The pyrimidine radicals in generation, substituted or unsubstituted triazine radical or substituted or unsubstituted benzimidazolyl, wherein substituent group are cyanogen
Base, phenyl, the triazine radical by phenyl substitution or the benzimidazolyl by phenyl substitution.
6. organic compound according to claim 1, which is characterized in that the compound indicated by the chemical formula 1 is selected from
Following compound,
7. a kind of organic luminescent device, which is characterized in that include organic compound described in claim 1.
8. organic luminescent device according to claim 7, which is characterized in that the organic luminescent device includes electron transmission
Layer, hole blocking layer include the two simultaneously, and the organic compound is included in the electron transfer layer, the hole hinders
Barrier is included in the two simultaneously.
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| KR1020150191146A KR20170080006A (en) | 2015-12-31 | 2015-12-31 | A novel organic compound and an organic light emitting diode comprising the same |
| PCT/KR2016/015465 WO2017116156A1 (en) | 2015-12-31 | 2016-12-29 | Novel organic compound and organic light emitting device containing same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103319532A (en) * | 2012-03-19 | 2013-09-25 | 海洋王照明科技股份有限公司 | Organic semiconductor material, preparation method and electroluminescent device |
| CN104073244A (en) * | 2013-03-29 | 2014-10-01 | 海洋王照明科技股份有限公司 | Bipolar phosphorescent host material and preparation method thereof as well as organic electroluminescent light emitting device |
| KR20150030616A (en) * | 2013-09-12 | 2015-03-20 | 주식회사 엘지화학 | Hetero-cyclic compound and organic electronic device comprising the same |
| KR20150037605A (en) * | 2013-09-30 | 2015-04-08 | 주식회사 엘지화학 | Organic light emitting device and method for preparing the same |
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| KR102249062B1 (en) * | 2014-11-28 | 2021-05-10 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| CN103319532A (en) * | 2012-03-19 | 2013-09-25 | 海洋王照明科技股份有限公司 | Organic semiconductor material, preparation method and electroluminescent device |
| CN104073244A (en) * | 2013-03-29 | 2014-10-01 | 海洋王照明科技股份有限公司 | Bipolar phosphorescent host material and preparation method thereof as well as organic electroluminescent light emitting device |
| KR20150030616A (en) * | 2013-09-12 | 2015-03-20 | 주식회사 엘지화학 | Hetero-cyclic compound and organic electronic device comprising the same |
| KR20150037605A (en) * | 2013-09-30 | 2015-04-08 | 주식회사 엘지화학 | Organic light emitting device and method for preparing the same |
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Application publication date: 20180831 |