CN103492528A - 芘衍生物、有机发光介质、以及包含它们的有机电致发光元件 - Google Patents
芘衍生物、有机发光介质、以及包含它们的有机电致发光元件 Download PDFInfo
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- CN103492528A CN103492528A CN201280018765.7A CN201280018765A CN103492528A CN 103492528 A CN103492528 A CN 103492528A CN 201280018765 A CN201280018765 A CN 201280018765A CN 103492528 A CN103492528 A CN 103492528A
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- aryl
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- 150000003220 pyrenes Chemical class 0.000 title claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 192
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 141
- 150000001721 carbon Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 36
- -1 benzo anthryl Chemical group 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 33
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 241001597008 Nomeidae Species 0.000 claims description 16
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
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- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 2
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- 239000010410 layer Substances 0.000 description 102
- 239000000463 material Substances 0.000 description 46
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- 238000000034 method Methods 0.000 description 19
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- 238000002347 injection Methods 0.000 description 17
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
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- 150000004646 arylidenes Chemical group 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 0 CCC(C1)C1(C)C(C)CCCC1C(C)*CC1 Chemical compound CCC(C1)C1(C)C(C)CCCC1C(C)*CC1 0.000 description 3
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- 238000004020 luminiscence type Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
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- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
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- VXGBQDMZTPOHNI-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12 VXGBQDMZTPOHNI-UHFFFAOYSA-N 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- CUIWZLHUNCCYBL-UHFFFAOYSA-N decacyclene Chemical compound C12=C([C]34)C=CC=C4C=CC=C3C2=C2C(=C34)C=C[CH]C4=CC=CC3=C2C2=C1C1=CC=CC3=CC=CC2=C31 CUIWZLHUNCCYBL-UHFFFAOYSA-N 0.000 description 1
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- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
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- 230000009467 reduction Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
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- 230000008313 sensitization Effects 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005259 triarylamine group Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation 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
- 238000007740 vapor deposition 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
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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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Abstract
本发明提供一种有机发光介质,其包含下述式(1)所示的芘衍生物及下述式(2)所示的苯基取代蒽衍生物。[Ar1~Ar4各自独立地为取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基]
Description
技术领域
本发明涉及芘衍生物、有机发光介质、以及包含它们的有机电致发光元件。
背景技术
使用了有机物质的有机电致发光(EL)元件被视为有望用作固体发光型的廉价的大面积全色显示元件,进行了很多的开发。一般来说,有机EL元件由发光层及夹持该层的一对对置电极构成。如下进行发光,即,当对两电极间施加电场时,即会从阴极侧注入电子,从阳极侧注入空穴。继而,该电子在发光层中与空穴再结合,生成激发态,在激发态返回到基态时将能量以光的形式放出。
最近的有机EL元件因长寿命化技术的发展而正逐渐应用于手提电话、电视机等的全色显示器中,在该过程中,通过发光材料的改良而使有机EL元件的性能慢慢地得到改善。
例如,专利文献1~3中,公开了特定的结构的蒽主体与二氨基芘掺杂剂的组合,然而需要进一步提高发光特性(高发光效率、长寿命等)。
现有技术文献
专利文献
专利文献1:WO2004/018587号小册子
专利文献2:日本特开2004-204238号公报
专利文献3:WO2005/108348号小册子
发明内容
发明所要解决的课题
本发明是为了解决上述问题而完成的,其目的在于,提供一种高效率·长寿命的有机EL元件。
用于解决课题的方法
本发明人等发现,使用了在特定的位置具有特定的结构的芘衍生物、和苯基取代蒽衍生物的有机发光介质显示出高发光效率,并且寿命长。此外还发现,将包含该有机发光介质的有机薄膜用于发光层中的有机电致发光元件是高效率并且长寿命的元件,从而完成了本发明。
根据本发明,提供以下的有机发光介质、有机薄膜及有机电致发光元件。
1.一种有机发光介质,其包含下述式(1)所示的芘衍生物及下述式(2)所示的苯基取代蒽衍生物。
式(1)中,Ar1~Ar4各自独立地为取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
X1~X8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、取代或未取代的成环碳数为6~30的芳烷基、卤素原子、或者取代或未取代的碳数为1~20的卤代烷基,
R1~R8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、或者取代或未取代的成环碳数为6~30的芳烷基,
R1与R2、R2与R3、R3与R4、R5与R6、R6与R7及R7与R8可以分别相互结合而形成取代或未取代的烃环、或者取代或未取代的杂环。
式(2)中,Ar11是取代或未取代的成环碳数为6~30的亚芳基、或者取代或未取代的成环原子数为5~20的亚杂芳基,
m是0~3的整数,在m为0的情况下Ar11是单键,
Ar12是取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
n是1~3的整数,
在m或n为2以上的情况下,多个Ar11及Ar12各自既可以相同也可以不同。
2.根据1所述的有机发光介质,其中,X1~X8是氢原子。
3.根据1所述的有机发光介质,其中,X2及X6是取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、或者取代或未取代的成环碳数为3~20的环烷基,X1、X3~X5、X7及X8是氢原子。
4.根据1~3中任一项所述的有机发光介质,其中,Ar3及Ar4是取代或未取代的成环碳数为6~30的芳基。
5.根据1~4中任一项所述的有机发光介质,其中,R3及R7、或者R2及R6是取代或未取代的成环碳数为6~30的芳基。
6.根据4或5所述的有机发光介质,其中,Ar3及Ar4是取代或未取代的苯基。
7.根据5或6所述的有机发光介质,其中,R3及R7、或者R2及R6是取代或未取代的苯基。
8.根据1~7中任一项所述的有机发光介质,其中,m是1,并且n是1。
9.根据1~7中任一项所述的有机发光介质,其中,m是0,并且n是1。
10.根据8所述的有机发光介质,其中,Ar11是取代或未取代的成环碳数为6~18的亚芳基、或者取代或未取代的成环原子数为5~20的亚杂芳基,Ar12是取代或未取代的成环碳数为6~18的芳基、或者取代或未取代的成环原子数为5~20的杂芳基。
11.根据9所述的有机发光介质,其中,Ar12是取代或未取代的成环碳数为6~18的芳基或者取代或未取代的成环原子数为5~20的杂芳基。
12.根据10所述的有机发光介质,其中,Ar11是取代或未取代的亚苯基、或者取代或未取代的亚萘基。
13.根据11所述的有机发光介质,其中,Ar12是取代或未取代的萘基、取代或未取代的苯并蒽基、取代或未取代的苯并菲基、取代或未取代的菲基、或者取代或未取代的二苯并呋喃基。
14.根据12所述的有机发光介质,其中,Ar11是取代或未取代的亚苯基,Ar12是取代或未取代的萘基。
15.一种芘衍生物,其以下述式(10)表示。
式(10)中,Ar1~Ar6各自独立地为取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
X1~X8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、取代或未取代的成环碳数为6~30的芳烷基、卤素原子、或者取代或未取代的碳数为1~20的卤代烷基,
R11、R12、R14~R16及R18各自独立地为氢原子、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、或者取代或未取代的成环碳数为6~30的芳烷基。
16.一种有机电致发光元件,其是在阴极与阳极之间夹持有包括发光层的1层以上的有机薄膜层的有机电致发光元件,
其中,上述发光层包含1~14中任一项所述的有机发光介质或者15所述的芘衍生物。
根据本发明,可以提供高效率·长寿命的有机发光介质、有机薄膜及有机EL元件。
具体实施方式
以下,对本发明的有机发光介质及有机电致发光元件进行详细说明。
I.有机发光介质
本发明的有机发光介质的特征在于,包含下述式(1)所示的芘衍生物及下述式(2)所示的苯基取代蒽衍生物。
这里,式(1)所示的芘衍生物作为掺杂材料(掺杂剂)来发挥作用,下述式(2)所示的苯基取代蒽衍生物作为主体材料来发挥作用。
式(I)中,Ar1~Ar4各自独立地为取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
X1~X8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、取代或未取代的成环碳数为6~30的芳烷基、卤素原子、或者取代或未取代的碳数为1~20的卤代烷基,
R1~R8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、或者取代或未取代的成环碳数为6~30的芳烷基,
R1与R2、R2与R3、R3与R4、R5与R6、R6与R7及R7与R8可以分别相互结合而形成取代或未取代的烃环、或者取代或未取代的杂环。]
式(2)中,Ar11是取代或未取代的成环碳数为6~30的亚芳基(芳香族烃基)、或者取代或未取代的成环原子数为5~20的亚杂芳基(芳香族杂环基),
m是0~3的整数,在m为0的情况下Ar11是单键,
Ar12是取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
n是1~3的整数,
在m或者n为2以上的情况下,多个Ar11及Ar12各自既可以相同也可以不同。
以下,对于上述式(1)及式(2)中的各取代基,举出具体例等来进行说明。
本说明书中,所谓“成环碳”,是指构成包含碳和氢的、饱和脂肪族环式结构、不饱和脂肪族环式结构、或者芳香族烃环式结构的碳原子。所谓“成环原子”,是指构成包含杂原子的、饱和脂肪族环式结构、不饱和脂肪族环式结构、以及芳香族杂环式结构的碳原子及杂原子。
另外,“烃环”包括包含碳和氢的、饱和脂肪族环式结构、不饱和脂肪族环式结构、或者芳香族烃环式结构,“杂环”包括包含杂原子的、饱和脂肪族环式结构、不饱和脂肪族环式结构、以及芳香族杂环式结构。
本说明书中,在构成式(1)所示的芘衍生物及式(2)所示的苯基取代蒽衍生物的全部的原子中包括所对应的同位素。
Ar1~Ar4、X1~X8及R1~R8及Ar12中的成环碳数为6~30的芳基中,包括成环碳数为6~30的非稠合芳香族烃环基、成环碳数为10~30的稠合芳香族烃环基及成环碳数为9~30的环集合芳香族烃环基。这里,所谓“非稠合芳香族烃环”,是指将多个芳香族环(单环和/或稠合环)以单键进行结合而成的基团,所谓“稠合芳香族烃环”,是指将多个芳香族环以2个以上的共用的成环碳原子进行结合而成的环,所谓“环集合芳香族烃环”,是指将芳香族环与脂肪族环以2个以上的共用的成环碳原子进行结合而成的环。
作为成环碳数为6~30的芳基的具体例,可以举出苯基、萘基、蒽基、菲基、并四苯基、芘基、基、芴基、苯并[c]菲基、苯并[g]基、苯并[9,10]菲基(triphenylenyl)、9,9一二甲基芴基、苯并芴基、二苯并芴基、联苯基、三联苯基、荧蒽基等。上述的芳基当中,特别优选苯基、联苯基、甲苯基、二甲苯基、萘基。上述芳基的成环碳数优选为6~18,更优选为6~10。
Ar1~Ar4及Ar12中的成环原子数为5~20的杂芳基包括成环原子数为5~20的非稠合芳香族杂环基、以及成环原子数为10~20的稠合芳香族杂环基及成环原子数为9~20的环集合芳香族杂环基。这里,所谓“非稠合芳香族杂环”,是指将包含1个以上的芳香族杂环的2个以上的芳香族环(单环和/或稠合环)以单键进行结合而成的基团,所谓“稠合芳香族杂环”,是指将包含1个以上的芳香族杂环的2个以上的芳香族环以2个以上的共用的成环原子进行结合而成的环,所谓“环集合芳香族烃环”,是指将1个以上的芳香族杂环和脂肪族环以2个以上的共用的碳原子进行结合而成的环。
作为成环原子数为5~20的杂芳基的具体例,可以举出吡咯基、吡嗪基、吡啶基、吲哚基、异吲哚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、喹啉基、异喹啉基、喹喔啉基、咔唑基、菲啶基、吖啶基、菲酮基(phenanthronyl group)、吩嗪基、吩噻嗪基、吩噁嗪基、噁唑基、噁二唑基、呋咱基、噻吩基、2甲基吡咯基、三嗪基、嘧啶基等。优选为二苯并呋喃基、二苯并噻吩基、咔唑基。上述杂芳基的成环原子数优选为5~14。
作为X1~X8及R1~R8中的碳数为1~20的烷基,可以举出甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基、正庚基、正辛基等。其中优选甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基。碳数优选为1~10,更优选为1~8,进一步优选为1~6。
作为X1~X8及R1~R8中的成环碳数为3~20的环烷基,可以举出环丙基、环丁基、环戊基、环己基、1-金刚烷基、2-金刚烷基、1-降冰片基、2-降冰片基等。成环碳数优选为3~10,更优选为3~8,进一步优选为3~6。
作为X1~X8及R1~R8中的被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基,可以举出如下的例子。
被烷基取代后的甲硅烷基可以表示为-SiY3,作为Y,可以举出上述的碳数为1~20的烷基的例子,具体来说,可以举出三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、丙基二甲基甲硅烷基等。
被芳基取代后的甲硅烷基可以表示为-SiZ3,作为Z,可以举出上述的成环碳数为6~30的芳基的例子当中的成环碳数为6~18的芳基,具体来说,可以举出三苯基甲硅烷基、苯基二甲基甲硅烷基、叔丁基二苯基甲硅烷基、三甲苯基甲硅烷基、三(二甲苯基)甲硅烷基等。
被烷基及芳基取代后的甲硅烷基可以表示为-SiYnZ(3-n)(n是1或2),作为Y,可以举出上述的碳数为1~20的烷基的例子,作为Z,可以举出上述的成环碳数为6~30的芳基的例子当中的成环碳数为6~18的芳基,具体例如上所述。
X1~X8及R1~R8中的碳数为1~20的烷氧基可以表示为-OY,作为Y,可以举出上述的碳数为1~20的烷基的例子,具体来说,可以举出甲氧基、乙氧基、丁氧基等。
X1~X8及R1~R8中的成环碳数为6~30的芳氧基可以表示为-OZ,作为Z,可以举出上述的成环碳数为6~30的芳基的例子,具体来说,可以举出苯氧基等。
X1~X8及R1~R8中的成环碳数为6~30的芳烷基可以表示为-Y-Z,作为Y,可以举出与上述的碳数为1~20的烷基的例子相对应的亚烷基的例子,作为Z,可以举出上述的成环碳数为6~30的芳基的例子。具体来说,可以举出苄基、苯基乙基、2-苯基丙烷-2-基等。
作为X1~X8中的卤素原子,可以举出氟、氯、溴、碘等,优选为氟原子。
作为X1~X8中的碳数为1~20的卤代烷基,优选碳数为1~20的氟化烷基,具体来说,可以举出氟甲基、二氟甲基、三氟甲基、氟乙基、三氟甲基甲基等。
Ar11中的成环碳数为6~30的亚芳基,可以表示为-Z-,作为Z,可以举出与上述的成环碳数为6~30的芳基的例子相对应的亚芳基。
Ar11中的成环原子数为5~20的亚杂芳基可以表示为-P-,作为P,可以举出与上述的成环原子数为5~20的杂芳基的例子相对应的亚杂芳基。
另外,作为“取代或未取代的”上述各基团中的取代基,可以举出如上所述的碳数为1~20的烷基、被碳数为1~20的烷基和/或成环碳数为6~18的芳基取代后的甲硅烷基、碳数为1~20的烷氧基、碳数为1~20的卤代烷基、碳数为1~20的卤代烷氧基、成环碳数为6~30的芳基、成环原子数为5~20的杂芳基、成环碳数为6~30的芳氧基、成环碳数为6~30的芳烷基、碳数为3~20的环烷基及氰基、羧基、碳数为1~20的羰基化合物、氟原子、碳数为1~20的卤代烷基等。
另外,上述式(1)中,R1与R2、R2与R3、R3与R4、R5与R6、R6与R7及R7与R8可以分别相互结合而形成取代或未取代的烃环、或者取代或未取代的杂环。在所形成的具体的烃环中,有萘基、菲基、芘基、9,9-二甲基芴基等。在所形成的具体的杂环中,有苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、1-芳基吲哚基、9-芳基咔唑基等。
上述式(2)中,m表示Ar11的重复数,是0~3的整数,优选为0~2的整数。在m为2以上的情况下,多个Ar11彼此既可以相同也可以不同。另外,在m为0的情况下,Ar11变为单键。
上述式(2)中,m为1~3时,n表示Ar12对Ar11的取代数,是1~3的整数,优选为1~2的整数。在n为2以上的情况下,多个Ar12彼此既可以相同也可以不同。m为0时,n为1,Ar12与蒽骨架结合。
优选在上述式(1)中,X2是取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~10的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、或者取代或未取代的成环碳数为6~30的芳基,X1、X3~X8是氢原子。
作为其他的优选的方式,在上述式(1)中,X2及X6是取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~10的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、或者取代或未取代的成环碳数为6~30的芳基,X1、X3、X4、X5、X7、X8是氢原子。
X2及X6的取代或未取代的碳数为1~20的烷基优选为碳数为1~6的烷基。X2及X6的被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基优选为取代或未取代的碳数为3~20的烷基甲硅烷基,更优选为碳数为3~12的烷基甲硅烷基。
作为其他的优选的方式,在上述式(1)中,X1~X8是氢原子。
优选在上述式(1)中,X2及X6是取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、或者取代或未取代的成环碳数为3~20的环烷基,X1、X3~X5、X7及X8是氢原子。
优选在上述式(1)中,Ar3及Ar4是取代或未取代的成环碳数为6~30的芳基。
优选在上述式(1)中,R3及R7、或者R2及R6是取代或未取代的成环碳数为6~30的芳基。该情况下,优选其他的R1~R8是氢。
优选在上述式(1)中,Ar3及Ar4是取代或未取代的苯基。
优选在上述式(1)中,R3及R7、或者R2及R6是取代或未取代的苯基。该情况下,优选其他的R1~R8是氢。
优选在上述式(1)中,从合成的容易度等考虑,Ar1与Ar2、Ar3与Ar4、R1与R5、R2与R6、R3与R7、R4与R8、X1与X5、X2与X6、X3与X7、X4与X8中的至少1组以上、更优选全部都相同(成为点对称)。
优选在上述式(2)中,m是1,并且n是1。
此时,优选Ar11是取代或未取代的成环碳数为6~18的亚芳基或者取代或未取代的成环原子数为5~20的亚杂芳基,Ar12是取代或未取代的成环碳数为6~18的芳基或者取代或未取代的成环原子数为5~20的杂芳基。
更优选Ar11是取代或未取代的亚苯基、或者取代或未取代的亚萘基。
进一步优选Ar11是取代或未取代的亚苯基,Ar12是取代或未取代的萘基。
优选在上述式(2)中,m是0,并且n是1。
此时,优选Ar12是取代或未取代的成环碳数为6~18的芳基、或者取代或未取代的成环原子数为5~20的杂芳基。
此外,更优选Ar12是取代或未取代的萘基、取代或未取代的苯并蒽基、取代或未取代的苯并菲基、取代或未取代的菲基、或者取代或未取代的二苯并呋喃基。
将本发明的有机发光介质中所用的上述式(1)所示的芘衍生物的优选的具体例化合物表示如下。
本发明还提供以下的式(10)的化合物。在有机发光介质中,可以与式(2)的衍生物一起,使用该式(10)的化合物。该情况下,式(2)的衍生物作为主体材料来发挥作用,式(10)的化合物作为掺杂剂材料来发挥作用。
式(10)中,Ar1~Ar4、X1~X8与式(1)的Ar1~Ar4、X1~X8分别相同,因而省略说明。
Ar5、Ar6与式(1)的Ar1~Ar4相同,因而省略说明。
R11、R12、R12~R16及R18各自独立地为氢原子、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、或者取代或未取代的成环碳数为6~30的芳烷基。
R11、R12、R14~R16及R18的碳数为1~20的烷基、成环碳数为3~20的环烷基、被碳数为1~20的烷基和/或成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、成环碳数为6~30的芳烷基、以及取代在这些基团上的取代基,与式(1)的对应的基团及其取代基分别相同,因而省略说明。
而且,在式(1)的衍生物的合适例的说明中,对于Ar1~Ar4、X1~X8,也适用于式(10)的衍生物。
对于Ar5、Ar6,优选为取代或未取代的成环碳数为6~30的芳基,更优选为取代或未取代的苯基。
对于R11、R12、R14~R16及R18,优选为氢。
另外,优选R12及R16优选是取代或未取代的成环碳数为6~30的芳基,更优选是取代或未取代的苯基。该情况下,优选其他的R11、R12、R14~R16及R18为氢。
在间位结合有Ar5和Ar6(特别是苯基)的上述式(10)的化合物与在对位结合有Ar5和Ar6的化合物相比,相对于胺部分来说的共轭体系的展宽小,另外向胺部的供电子性也被抑制得较低,因此存在短波长化的趋势,因而色纯度提高。另外可以认为,在分子结构中,在三维方面上平面性提高,可以有效地进行与主体原子的能量交换,因而存在效率提高的趋势。
将本发明的有机发光介质中使用的上述式(2)所示的苯基取代蒽衍生物的优选的具体例化合物表示如下。
将上述式(1)所示的芘衍生物中的至少一种作为掺杂材料(掺杂剂)来使用、并且将上述式(2)所示的苯基取代蒽衍生物中的至少一种作为主体材料来使用的有机发光介质具有发光效率高、寿命长的特性,通过作为有机电致发光元件等的发光层使用,而可得到发光效率高、寿命长的元件。
而且,在本发明的有机发光介质中,为了不损害其效果地制成更高效率且长寿命的发光介质,可以在上述芘衍生物及苯基取代蒽衍生物之外,还含有各种的材料。对于可以含有的材料,将在后面的本发明的有机电致发光元件的说明中进行叙述。
II.有机电致发光元件
本发明的有机电致发光元件(以下称作本发明的有机EL元件在阴极与阳极之间夹持有至少包括发光层的1层以上的有机薄膜层。
发光层包含本发明的有机发光介质或式(10)的芘衍生物。在发光层包含式(10)的芘衍生物时,作为主体材料优选还同时含有式(2)的衍生物。
本发明的有机EL元件中,发光层是具有发光功能的有机层,在采用掺杂体系的情况下,含有主体材料和掺杂剂材料。此时,主体材料主要具有促进电子与空穴的再结合、将激子关入到发光层内的功能,掺杂剂材料具有使在再结合中所得的激子有效地进行发光的功能。
向发光层中注入空穴的容易度和注入电子的容易度也可以不同,另外,发光层中的空穴和电子的以迁移率表示的空穴输送能力和电子输送能力也可以不同。
作为形成有机薄膜层的方法,例如可以应用蒸镀法、旋涂法、LB法等公知的方法。在将树脂等粘结剂和材料化合物溶于溶剂中而制成溶液后,也可以通过将其利用旋涂法等进行薄膜化,从而形成有机薄膜层。
在形成多层有机薄膜层的情况下,既可以仅利用相同的方法来形成,也可以使用两种或者两种以上的方法来形成。
本发明中,作为具有多层有机薄膜层的有机EL元件,可以举出以(阳极/空穴注入层/发光层/阴极)、(阳极/发光层/电子注入层/阴极)、(阳极/空穴注入层/发光层/电子注入层/阴极)、(阳极/空穴注入层/空穴输送层/发光层/电子注入层/阴极)、(阳极/空穴注入层/空穴输送层/发光层/电子输送层/电子注入层/阴极)等构成加以层叠而成的元件。
本发明的有机EL元件可以设为具有至少2层发光层的串列元件构成。将具体的构成的例子表示如下。
阳极/第一发光层/中间层/第二发光层/电子输送区域/阴极
阳极/第一发光层/电子输送区域/中间层/第二发光层/阴极
阳极/第一发光层/电子输送区域/中间层/第二发光层/电子输送区域/阴极
阳极/第一发光层/中间层/第二发光层/电子输送区域/阴极
阳极/第一发光层/电子输送区域/中间层/第二发光层/阴极
阳极/第一发光层/电荷阻挡层/第二发光层/电子输送区域/阴极
阳极/第一发光层/电荷阻挡层/第二发光层/第三发光层/电子输送区域/阴极
本发明的有机发光介质或式(10)的芘衍生物可以用于这些发光层中的一层或者2层以上的发光层中。另外,其他的发光层可以采用其他的使用了荧光发光性的材料的有机发光介质或使用了磷光发光性的材料的有机发光介质。
有机EL元件通过将有机薄膜层设为多层结构,从而可以防止由猝灭所造成的亮度或寿命的降低。空穴注入层、发光层、电子注入层也可以分别以二层以上的层构成来形成。此时,在空穴注入层的情况下,将从电极注入空穴的层称作空穴注入层,将从空穴注入层接受空穴并将空穴输送到发光层的层称作空穴输送层。同样地,在电子注入层的情况下,将从电极注入电子的层称作电子注入层,将从电子注入层接受电子并将电子输送到发光层的层称作电子输送层。这些层可以根据材料的能级、耐热性、与有机层或金属电极的密合性等各种要因来选择使用。
作为不使用本发明的有机发光介质或式(10)的芘衍生物的发光层中可以使用的材料,例如可以举出萘、菲、红荧烯、蒽、并四苯、芘、苝、、十环烯、晕苯、四苯基环戊二烯、五苯基环戊二烯、芴、螺芴等稠合多环芳香族化合物及它们的衍生物,三(8-羟基喹啉)铝等有机金属络合物,三芳基胺衍生物、苯乙烯基胺衍生物、芪衍生物、香豆素衍生物、吡喃衍生物、噁嗪酮衍生物、苯并噻唑衍生物、苯并噁唑衍生物、苯并咪唑衍生物、吡嗪衍生物、肉桂酸酯衍生物、二酮吡咯并吡咯衍生物、吖啶酮衍生物、喹吖啶酮衍生物等。
上述的化合物在不损害本发明的目的的范围内,也可以加入到使用了本发明的有机发光介质或式(10)的芘衍生物的发光层中使用。
作为空穴注入材料,优选具有输送空穴的能力,具有来自阳极的空穴注入效果、对发光层或发光材料来说优异的空穴注入效果,并且薄膜形成能力优异的化合物。具体来说,可举出酞菁衍生物、萘酞菁衍生物、卟啉衍生物、联苯胺型三苯基胺、二胺型三苯基胺、六氰基六氮杂苯并[9,10]菲等、和它们的衍生物、以及聚乙烯基咔唑、聚硅烷、导电性高分子等高分子材料,然而并不限定于此。
本发明的有机EL元件中可以使用的空穴注入材料当中,更有效的空穴注入材料是酞菁衍生物。
作为酞菁(Pc)衍生物,例如有H2Pc、CuPc、CoPc、NiPc、ZnPc、PdPc、FePc、MnPc、ClAlPc、ClGaPc、ClInPc、ClSnPc、Cl2SiPc、(HO)AlPc、(HO)GaPc、VOPc、TiOPc、MoOPc、GaPc-O-GaPc等酞菁衍生物及萘酞菁衍生物,然而并不限定于它们。
另外,也可以通过向空穴注入材料中添加TCNQ衍生物等电子接收物质来使载流子敏化。
本发明的有机EL元件中可以使用的优选的空穴输送材料是芳香族叔胺衍生物。
作为芳香族叔胺衍生物,例如为N,N’-二苯基-N,N’-二萘基-1,1’-联苯-4,4’-二胺、N,N,N’,N’-四联苯-1,1’-联苯-4,4’-二胺等、或者具有这些芳香族叔胺骨架的低聚物或聚合物,然而并不限定于它们。
作为电子注入材料,优选具有输送电子的能力,具有来自阴极的电子注入效果、对于发光层或者发光材料来说优异的电子注入效果,并且薄膜形成能力优异的化合物。
本发明的有机EL元件中,更有效的电子注入材料是金属络合物化合物及含氮杂环衍生物。
作为上述金属络合物化合物,例如可以举出8-羟基喹啉锂、双(8-羟基喹啉)锌、三(8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌等,然而并不限定于它们。
作为上述含氮杂环衍生物,例如优选为噁唑、噻唑、噁二唑、噻二唑、三唑、吡啶、嘧啶、三嗪、菲咯啉、苯并咪唑、咪唑并吡啶等,其中优选为苯并咪唑衍生物、菲咯啉衍生物、咪唑并吡啶衍生物。
作为优选的方式,在这些电子注入材料中还含有掺杂剂,为了使来自阴极的电子的接收变得容易,更优选在第二有机层的阴极界面附近掺杂以碱金属为代表的掺杂剂。
作为掺杂剂,可以举出给予体性金属、给予体性金属化合物及给予体性金属络合物,这些还原性掺杂剂既可以单独使用1种,也可以组合使用2种以上。
另外,为了提高根据本发明所得到的有机EL元件对于温度、湿度、气氛等的稳定性,也可以在元件的表面设置保护层,或利用硅油、树脂等保护元件整体。
作为本发明的有机EL元件的阳极所使用的导电性材料,适合为具有大于4eV的功函数的材料,可以使用碳、铝、钒、铁、钴、镍、钨、银、金、铂、钯等及它们的合金,ITO基板、NESA基板中使用的氧化锡、氧化铟等氧化金属,以及聚噻吩或聚吡咯等有机导电性树脂。
作为阴极中使用的导电性物质,适合为具有小于4eV的功函数的物质,可以使用镁、钙、锡、铅、钛、钇、锂、钌、锰、铝、氟化锂等及它们的合金,然而并不限定于它们。作为合金,可以举出作为代表例的镁/银、镁/铟、锂/铝等,然而并不限定于它们。合金的比率可以利用蒸镀源的温度、气氛、真空度等来控制,选择为适当的比率。如果需要,也可以通过二层以上的层构成来形成阳极及阴极。
对于本发明的有机EL元件,为了高效地发光,优选使至少一个面在元件的发光波长区域中充分透明。另外,优选基板也是透明的。透明电极是使用上述的导电性材料,利用蒸镀或溅射等方法,以确保规定的透光性的方式而加以设定的。对于发光面的电极,优选将光透过率设为10%以上。基板只要是具有机械强度、热强度且具有透明性的材料,就没有限定,有玻璃基板及透明性树脂膜。
本发明的有机EL元件的各层的形成可以应用真空蒸镀、溅射、等离子体、离子镀敷等干式成膜法或旋涂法、浸涂法、流涂法等湿式成膜法中的任一种方法。膜厚没有特别限定,然而需要设定为合适的膜厚。如果膜厚过厚,则为了获得一定的光输出,而需要大的施加电压,因而效率变差。如果膜厚过薄,则会产生小孔等,因而即使施加电场也无法获得充分的发光亮度。通常的膜厚适合为5nm~10μm的范围,而进一步优选为10nm~0.2μm的范围。
在湿式成膜法的情况下,将形成各层的材料溶解或分散于乙醇、氯仿、四氢呋喃、二噁烷等恰当的溶剂中而形成薄膜,该溶剂可以是任意一种。
作为适于此种湿式成膜法的溶液,可以使用含有式(1)所示的芘衍生物、式(2)所示的苯基取代蒽衍生物及溶剂作为有机EL材料的、含有有机EL材料的溶液。
无论在哪种有机薄膜层中,为了提高成膜性、防止膜中产生小孔等,均可以使用恰当的树脂或添加剂。
[实施例]
下面,通过举出实施例及比较例来对本发明进行更具体的说明,然而本发明并不受这些实施例的任何限定。
合成例:化合物D-1的合成
依照下述流程,合成出化合物D-1。
(a)2,5-二苯基苯胺的合成
将2,5-二溴苯胺(150g、0.598mol)、苯基硼酸(160g、1.79mol)、四(三苯基膦)钯(0)(27.6g、0.0234mol)、2M碳酸钠水溶液(900mL、1.80mol)及1,2-二甲氧基乙烷(3.5L)的混合物在氩气气氛下,在75℃下搅拌23小时。将反应混合物冷却到室温,加入水,过滤出析出的固体。将所得的固体用硅胶柱色谱法加以提纯,得到119g(81%)的作为目标的2,5-二苯基苯胺。
(b)N-苯基-2,5-二苯基苯胺的合成
将溴苯(36.4g、232mmol)、(a)中合成的2,5-二苯基苯胺(114g、464mmol)、乙酸钯(II)(1.56g、6.96mmol)、BINAP(2,2’-双(二苯基膦基)-1,1’-联萘)外消旋体、8.67g、13.9mmol)及甲苯1.5L的混合物,在氩气气流下加热到90℃,加入叔丁醇钠(44.6g、464mmol)后,在氩气气氛下在105℃下进行5小时搅拌。将反应混合物冷却到室温,加入水而进行分液。将所得的有机层的溶剂减压浓缩,将所得的固体用硅胶柱色谱法提纯,得到66.6g(收率85%)的作为目标的N-苯基-2,5-二苯基苯胺。
(c)化合物D-1的合成
将1,6-二溴芘(23.2g、64.5mmol)、(b)中合成的N-苯基-2,5-二苯基苯胺(45.6g、142mmol)、乙酸钯(0.6g、2.67mmol)、三叔丁基膦(1.08g、5.33mmol)及甲苯(700m1)的混合物在氩气气流下加热到90℃,加入叔丁醇钠(15.4g、160mmol)后,在氩气气氛下在105℃下进行3小时搅拌。将反应混合物冷却到室温,过滤出提纯了的固体。将所得的固体用硅胶色谱法提纯,然后通过重结晶进行提纯,得到33.7g(收率62%)的作为目标的化合物D-1。
对所得的化合物进行质谱分析,结果鉴定为化合物D-1(相对于分子量840.35,m/e=840)。
实施例1
在25mm×75mm×1.1mm尺寸的玻璃基板上,设置膜厚120nm的包含铟锡氧化物的透明电极。该透明电极作为阳极发挥作用。接下来,在对该玻璃基板照射紫外线及臭氧,进行清洗后,将该基板设置在真空蒸镀装置中。
在阳极上以50nm的厚度蒸镀化合物HT-1作为空穴注入层后,在其上以45nm的厚度蒸镀化合物HT-2作为空穴输送层。然后,以质量比25:5同时蒸镀作为主体材料的蒽衍生物EM-1和作为掺杂材料的化合物D-1,形成厚30nm的发光层。在该发光层上,以25nm的厚度蒸镀化合物ET-1作为电子注入层。然后,以1nm的厚度蒸镀氟化锂,然后以150nm的厚度蒸镀铝,制作出有机EL元件。而且,该铝/氟化锂作为阴极来发挥作用。
上述有机EL元件的制造中所用的化合物HT-1、化合物HT-2、化合物ET-1分别是具有下述结构的化合物。
对所得的有机EL元件,分别评价了在电流密度10mA/cm2下驱动时的元件性能(外部量子收率(%))、以及在电流密度50mA/cm2下从初期亮度降低至亮度为80%的寿命(小时)。将结果表示于表1中。
外部量子收率(E.Q.E.)的测定方法如下所示。
对所得的有机EL元件通入电流密度10mA/cm2的电流,用分光放射亮度计(CS1000:Minolta制)测定发光光谱,利用下述数学式算出外部量子收率。
NP:光子数
NE:电子数
π:圆周率=3.1416
λ:波长(nm)
h:普朗克常数=6.63×10-34(J·s)
c:光速度=3×108(m/s)
J:电流密度(mA/cm2)
e:电荷=1.6×10-19(C)
实施例2~15及比较例1~11
除了将掺杂材料及主体材料变更为表1所示的化合物以外,与实施例1相同地进行操作,制造出有机EL元件,评价了外部量子收率(%)及寿命(小时)。将结果示于表1中。
将各实施例及比较例中制造的有机EL元件的在发光层中作为掺杂材料及主体材料来使用的化合物的结构式表示如下。
(掺杂材料)
(主体材料)
[表1]
根据表1的结果可知,在将式(1)所示的芘衍生物作为掺杂材料、并且将式(2)所示的苯基取代蒽衍生物作为主体材料来组合使用的情况下,可以得到高的外部量子收率(%)和长的寿命。
本发明中,通过将具有特定结构的芘衍生物、具有特定结构的苯基取代蒽衍生物组合使用,从而使载流子平衡提高,其结果是,可认为可以制成高效率且长寿命的有机EL元件。
工业上的可利用性
本发明的有机发光介质在制造高效率并且长寿命的有机EL元件方面十分有用。
本发明的有机EL元件可以用于壁挂型电视机的平板显示器等的平面发光体,复印机、打印机、液晶显示器的背光灯或者计量仪器类的光源,显示板、标识等中。
另外,本发明的有机发光介质不仅可以用于有机EL元件,也可以在电子照片感光体、光电转换元件、太阳能电池、图像传感器等领域中使用。
虽然在上述内容中详细说明了若干个本发明的实施方式和/或实施例,然而对于本领域技术人员来说,很容易实质上不脱离本发明的新颖的指教及效果地对这些作为例示的实施方式和/或实施例施加很多变更。因而,上述很多的变更也包含在本发明的范围中。
将该说明书中所记载的文献的内容全部引用于此。
Claims (16)
1.一种有机发光介质,其包含下述式(1)所表示的芘衍生物及下述式(2)表示的苯基取代蒽衍生物,
式(1)中,Ar1~Ar4各自独立地为取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
X1~X8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、取代或未取代的成环碳数为6~30的芳烷基、卤素原子、或者取代或未取代的碳数为1~20的卤代烷基,
R1~R8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、或者取代或未取代的成环碳数为6~30的芳烷基,
R1与R2、R2与R3、R3与R4、R5与R6、R6与R7及R7与R8可以分别相互键合而形成取代或未取代的烃环、或者取代或未取代的杂环;
式(2)中,Ar11是取代或未取代的成环碳数为6~30的亚芳基、或者取代或未取代的成环原子数为5~20的亚杂芳基,
m是0~3的整数,在m为0的情况下Ar11是单键,
Ar12是取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
n是1~3的整数,
在m或者n为2以上的情况下,多个Ar11及Ar12各自可以相同、也可以不同。
2.根据权利要求1所述的有机发光介质,其中,
X1~X8是氢原子。
3.根据权利要求1所述的有机发光介质,其中,
X2及X6是取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、或者取代或未取代的成环碳数为3~20的环烷基,X1、X3~X5、X7及X8是氢原子。
4.根据权利要求1~3中任一项所述的有机发光介质,其中,
Ar3及Ar4是取代或未取代的成环碳数为6~30的芳基。
5.根据权利要求1~4中任一项所述的有机发光介质,其中,
R3及R7、或者R2及R6是取代或未取代的成环碳数为6~30的芳基。
6.根据权利要求4或5所述的有机发光介质,其中,
Ar3及Ar4是取代或未取代的苯基。
7.根据权利要求5或6所述的有机发光介质,其中,
R3及R7、或者R2及R6是取代或未取代的苯基。
8.根据权利要求1~7中任一项所述的有机发光介质,其中,
m是1,并且n是1。
9.根据权利要求1~7中任一项所述的有机发光介质,其中,
m是0,并且n是1。
10.根据权利要求8所述的有机发光介质,其中,
Ar11是取代或未取代的成环碳数为6~18的亚芳基、或者取代或未取代的成环原子数为5~20的亚杂芳基,Ar12是取代或未取代的成环碳数为6~18的芳基、或者取代或未取代的成环原子数为5~20的杂芳基。
11.根据权利要求9所述的有机发光介质,其中,
Ar12是取代或未取代的成环碳数为6~18的芳基、或者取代或未取代的成环原子数为5~20的杂芳基。
12.根据权利要求10所述的有机发光介质,其中,
Ar11是取代或未取代的亚苯基、或者取代或未取代的亚萘基。
13.根据权利要求11所述的有机发光介质,其中,
Ar12是取代或未取代的萘基、取代或未取代的苯并蒽基、取代或未取代的苯并菲基、取代或未取代的菲基、或者取代或未取代的二苯并呋喃基。
14.根据权利要求12所述的有机发光介质,其中,
Ar11是取代或未取代的亚苯基,Ar12是取代或未取代的萘基。
15.一种芘衍生物,其由下述式(10)表示,
式(10)中,Ar1~Ar6各自独立地为取代或未取代的成环碳数为6~30的芳基、或者取代或未取代的成环原子数为5~20的杂芳基,
X1~X8各自独立地为氢原子、取代或未取代的成环碳数为6~30的芳基、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、氰基、取代或未取代的碳数为1~20的烷氧基、取代或未取代的成环碳数为6~30的芳氧基、取代或未取代的成环碳数为6~30的芳烷基、卤素原子、或者取代或未取代的碳数为1~20的卤代烷基,
R11、R12、R14~R16及R18各自独立地为氢原子、取代或未取代的碳数为1~20的烷基、取代或未取代的成环碳数为3~20的环烷基、被取代或未取代的碳数为1~20的烷基和/或取代或未取代的成环碳数为6~18的芳基取代后的甲硅烷基或未取代的甲硅烷基、或者取代或未取代的成环碳数为6~30的芳烷基。
16.一种有机电致发光元件,其是在阴极与阳极之间夹持有包括发光层的1层以上的有机薄膜层的有机电致发光元件,其中,所述发光层包含权利要求1~14中任一项所述的有机发光介质或者权利要求15所述的芘衍生物。
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