WO2015102118A1 - 多環芳香族化合物 - Google Patents
多環芳香族化合物 Download PDFInfo
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- WO2015102118A1 WO2015102118A1 PCT/JP2015/054426 JP2015054426W WO2015102118A1 WO 2015102118 A1 WO2015102118 A1 WO 2015102118A1 JP 2015054426 W JP2015054426 W JP 2015054426W WO 2015102118 A1 WO2015102118 A1 WO 2015102118A1
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- formula
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- -1 Polycyclic aromatic compound Chemical class 0.000 title claims abstract description 201
- 239000000463 material Substances 0.000 claims abstract description 151
- 125000003118 aryl group Chemical group 0.000 claims abstract description 130
- 150000001875 compounds Chemical class 0.000 claims description 297
- 238000006243 chemical reaction Methods 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- 125000004432 carbon atom Chemical group C* 0.000 claims description 96
- 238000002347 injection Methods 0.000 claims description 83
- 239000007924 injection Substances 0.000 claims description 83
- 125000001072 heteroaryl group Chemical group 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 229910052751 metal Inorganic materials 0.000 claims description 38
- 239000002184 metal Substances 0.000 claims description 38
- 229910052782 aluminium Inorganic materials 0.000 claims description 35
- 230000005525 hole transport Effects 0.000 claims description 35
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
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- 150000002431 hydrogen Chemical class 0.000 claims description 14
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
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- 125000004104 aryloxy group Chemical group 0.000 claims description 10
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- 230000005669 field effect Effects 0.000 claims description 9
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- 125000005842 heteroatom Chemical group 0.000 claims description 9
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
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- 150000003222 pyridines Chemical class 0.000 claims description 4
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000003367 polycyclic group Chemical group 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 12
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 125000001424 substituent group Chemical group 0.000 description 41
- 239000007788 liquid Substances 0.000 description 40
- 238000000926 separation method Methods 0.000 description 40
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 40
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- 235000017281 sodium acetate Nutrition 0.000 description 30
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
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- 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 18
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 17
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 16
- 229910052744 lithium Inorganic materials 0.000 description 15
- 239000012046 mixed solvent Substances 0.000 description 15
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 14
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 13
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- 150000003568 thioethers Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- WGWZJNILGYTDHU-UHFFFAOYSA-K tris(3,5-dimethylphenoxy)alumane Chemical compound CC=1C=C([O-])C=C(C1)C.[Al+3].CC=1C=C([O-])C=C(C1)C.CC=1C=C([O-])C=C(C1)C WGWZJNILGYTDHU-UHFFFAOYSA-K 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
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- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
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Definitions
- the present invention relates to a polycyclic aromatic compound, an organic electroluminescence device using the same, an organic field effect transistor, an organic thin film solar cell, a display device, and an illumination device.
- the organic EL element has a structure composed of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers including an organic compound disposed between the pair of electrodes.
- the layer containing an organic compound include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons.
- Various organic materials suitable for these layers have been developed.
- a benzofluorene compound has been developed (International Publication No. 2004/061047).
- a hole transport material for example, a triphenylamine compound has been developed (Japanese Patent Laid-Open No. 2001-172232).
- an anthracene compound has been developed (Japanese Patent Laid-Open No. 2005-170911).
- the charge transport property of a NO-linked compound (Compound 1 on page 63) is evaluated, but a method for producing a material other than the NO-linked compound is not described, and the element to be linked is not described. Since the electronic state of the entire compound is different if it is different, the characteristics obtained from materials other than NO-linked compounds are not yet known. Other examples of such compounds can be found (WO 2011/107186).
- a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence having a shorter wavelength, and thus is useful as a blue light-emitting layer material.
- a compound having a novel conjugated structure having a large T1 is also required as an electron transport material or a hole transport material sandwiching the light emitting layer.
- the host material of the organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene and carbazole are connected by a single bond, phosphorus atom or silicon atom. This is because a large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material is secured by connecting a large number of relatively conjugated aromatic rings. Furthermore, a host material of an organic EL device using a phosphorescent material or a thermally activated delayed fluorescent material also requires high triplet excitation energy (E T ), but the molecule has a donor or acceptor aromatic ring or substituent.
- E T triplet excitation energy
- the present inventors have found a novel polycyclic aromatic compound in which a plurality of aromatic rings are linked by a boron atom and an oxygen atom, and succeeded in the production thereof. Further, the present inventors have found that an excellent organic EL element can be obtained by arranging an organic EL element by arranging the layer containing the polycyclic aromatic compound between a pair of electrodes, thereby completing the present invention. That is, the present invention provides a material for an organic EL device comprising the following polycyclic aromatic compound or multimer thereof, and further comprising the following polycyclic aromatic compound or multimer thereof.
- a ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
- Y 1 is B, P, P ⁇ O, P ⁇ S, Al, Ga, As, Si—R or Ge—R, wherein R in the Si—R and Ge—R is aryl or alkyl, X 1 and X 2 are each independently O, N—R, S or Se, and R in the N—R is an optionally substituted aryl, an optionally substituted heteroaryl or an alkyl.
- R in the N—R may be bonded to the A ring, B ring and / or C ring by a linking group or a single bond, and At least one hydrogen in the compound or structure represented by the formula (1) may be substituted with halogen or deuterium.
- a ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or Substituted with unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy
- these rings have a 5-membered or 6-membered ring that shares a bond with the fused bicyclic structure in the center of the above formula composed of Y 1 , X 1 and X 2 , Y 1 is B, P, P ⁇ O, P ⁇ S, Al, Ga, As, Si—R or Ge—R, wherein R in the Si—R
- R in the —C (—R) 2 — may be hydrogen or alkyl, At least one hydrogen in the compound or structure represented by formula (1) may be substituted with halogen or deuterium, and In the case of a multimer, it is a dimer or trimer having 2 or 3 structures represented by the general formula (1).
- X 1 and X 2 are each independently O, N—R, S or Se, wherein R in N—R is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms or carbon number 1 to 6 alkyl, and R in N—R is bonded to the a ring, b ring and / or c ring by —O—, —S—, —C (—R) 2 — or a single bond.
- R in the —C (—R) 2 — may be alkyl having 1 to 6 carbon atoms, and At least one hydrogen in the compound represented by the formula (2) may be substituted with halogen or deuterium.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl having 6 to 30 carbon atoms, carbon Heteroaryl or diarylamino having 2 to 30 (wherein aryl is aryl having 6 to 12 carbons), and adjacent groups of R 1 to R 11 are bonded to each other to form a ring, b ring or c
- the ring may form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring is substituted with an aryl having 6 to 10 carbon atoms.
- Y 1 is B, P, P ⁇ O, P ⁇ S or Si—R
- R in the Si—R is aryl having 6 to 10 carbon atoms or alkyl having 1 to 4 carbon atoms
- X 1 and X 2 are each independently O, N—R or S, wherein R in said N—R is aryl having 6 to 10 carbon atoms or alkyl having 1 to 4 carbon atoms, and At least one hydrogen in the compound represented by the formula (2) may be substituted with halogen or deuterium;
- organic device material according to [9], wherein the organic device material is an organic electroluminescent element material, an organic field effect transistor material, or an organic thin film solar cell material.
- An organic electroluminescent element comprising a pair of electrodes composed of an anode and a cathode, and a light emitting layer disposed between the pair of electrodes and containing the light emitting layer material described in [11] above.
- a pair of electrodes composed of an anode and a cathode; a light emitting layer disposed between the pair of electrodes; and a material for an electron injection layer described in [12] above and / or disposed between the cathode and the light emitting layer, and / or An organic electroluminescence device having an electron injection layer and / or an electron transport layer containing an electron transport layer material.
- a pair of electrodes composed of an anode and a cathode; a light-emitting layer disposed between the pair of electrodes; a material for a hole injection layer described in [13] above, disposed between the anode and the light-emitting layer; Or an organic electroluminescent element which has a positive hole injection layer and / or a positive hole transport layer containing the material for positive hole transport layers.
- the organic electroluminescence device according to any one of [14] to [16] above, which contains at least one selected from the group consisting of phenanthroline derivatives, borane derivatives, and benzimidazole derivatives.
- the electron transport layer and / or the electron injection layer further includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, or an alkaline earth metal. Containing at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes, 17].
- a display device comprising the organic electroluminescent element as described in any one of [14] to [18].
- a lighting device comprising the organic electroluminescent element according to any one of [14] to [18].
- a novel polycyclic aromatic compound that can be used as a material for an organic EL element for example, can be provided, and an excellent organic EL element can be obtained by using this polycyclic aromatic compound. Can be provided.
- a polycyclic aromatic compound in which aromatic rings are connected by heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur has a large HOMO-LUMO gap (band gap Eg in a thin film). It has been found that it has a high triplet excitation energy (E T ). This is because a 6-membered ring containing a hetero element has a low aromatic attribute, so that the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugated system is suppressed, and the triplet excited state (T1) due to the electronic perturbation of the hetero element This is considered to be caused by the localization of SOMO1 and SOMO2.
- the polycyclic aromatic compound containing a hetero element according to the present invention has triplet excitation because the exchange interaction between both orbitals becomes small due to localization of SOMO1 and SOMO2 in the triplet excited state (T1). Since the energy difference between the state (T1) and the singlet excited state (S1) is small and shows thermally activated delayed fluorescence, it is also useful as a fluorescent material for organic EL elements.
- a material having a high triplet excitation energy (E T ) is also useful as an electron transport layer or a hole transport layer of a phosphorescent organic EL device or an organic EL device using thermally activated delayed fluorescence.
- these polycyclic aromatic compounds can arbitrarily move the energy of HOMO and LUMO by introducing substituents, so that the ionization potential and electron affinity can be optimized according to the surrounding materials. .
- the present invention relates to a polycyclic aromatic compound represented by the following general formula (1) or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1). It is a multimer.
- the present invention is preferably a polycyclic aromatic compound represented by the following general formula (2) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by the following general formula (2).
- the A ring, B ring and C ring in the general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent.
- This substituent is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (with aryl Amino groups having heteroaryl), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy are preferred.
- substituents include aryl, heteroaryl and alkyl.
- the aryl ring or heteroaryl ring has a bond with a condensed bicyclic structure in the center of the general formula (1) composed of Y 1 , X 1 and X 2 (hereinafter, this structure is also referred to as “D structure”). It is preferable to have a 5-membered ring or a 6-membered ring shared.
- the “condensed bicyclic structure (D structure)” means that two saturated hydrocarbon rings composed of Y 1 , X 1 and X 2 shown in the center of the general formula (1) are condensed. Means structure.
- the “six-membered ring sharing a bond with the condensed bicyclic structure” means, for example, a ring (benzene ring (six-membered ring)) condensed to the D structure as shown in the general formula (2).
- the aryl ring or heteroaryl ring (which is A ring) has this 6-membered ring” means that the A ring is formed only by this 6-membered ring or includes this 6-membered ring.
- aryl ring or heteroaryl ring having a 6-membered ring means that a 6-membered ring constituting all or part of the A ring is condensed to the D structure.
- a ring (or B ring, C ring) in general formula (1) is the ring a and its substituents R 1 to R 3 (or b ring and its substituents R 4 to R 7 , c) in general formula (2).
- the general formula (2) corresponds to the case where “AC ring having a 6-membered ring” is selected as the A to C rings of the general formula (1). In that sense, each ring of the general formula (2) is represented by lower case letters a to c.
- adjacent groups of the substituents R 1 to R 11 of the a ring, b ring, and c ring are bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring, or c ring.
- at least one hydrogen in the ring formed may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy or aryloxy, and these At least one hydrogen in may be substituted with aryl, heteroaryl or alkyl.
- the polycyclic aromatic compound represented by the general formula (2) has the following formulas (2-1) and (2-2) depending on the mutual bonding form of the substituents in the a-ring, b-ring and c-ring. ),
- the ring structure constituting the compound changes.
- a ′ ring, B ′ ring and C ′ ring in each formula correspond to A ring, B ring and C ring in general formula (1), respectively.
- the A ′ ring, the B ′ ring and the C ′ ring are adjacent to the substituents R 1 to R 11 in the general formula (2).
- the aryl ring or heteroaryl ring formed together with the a ring, b ring and c ring, respectively the condensed ring formed by condensing another ring structure to the a ring, b ring or c ring. It can also be said).
- b-ring R 8 and c-ring R 7 , b-ring R 11 and a-ring R 1 , c-ring R 1 R 4 and R 3 in the a ring do not correspond to “adjacent groups” and they are not bonded. That is, “adjacent group” means an adjacent group on the same ring.
- the compounds represented by the formulas (2-1) and (2-2) are, for example, compounds represented by the formulas (1-2) to (1-17) listed as specific compounds described later. Correspond. That is, for example, an A ′ ring (or B ′ ring formed by condensing a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring with a benzene ring that is a ring (or b ring or c ring) Or a condensed ring A ′ (or a condensed ring B ′ or a condensed ring C ′) formed by a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively. is there.
- Y 1 in the general formula (1) is B, P, P ⁇ O, P ⁇ S, Al, Ga, As, Si—R or Ge—R, and R in Si—R and Ge—R is aryl. Or alkyl.
- the atom bonded to the A ring, B ring or C ring is P, Si or Ge.
- Y 1 is preferably B, P, P ⁇ O, P ⁇ S or Si—R, and particularly preferably B. This explanation is the same for Y 1 in the general formula (2).
- X 1 and X 2 in the general formula (1) are each independently O, N—R, S or Se, and R in the N—R is optionally substituted aryl or optionally substituted
- R in the “—C (—R) 2 —” is hydrogen or alkyl. This description is the same for X 1 and X 2 in the general formula (2).
- the definition that “R of N—R is bonded to the A ring, B ring and / or C ring by a linking group or a single bond” Corresponds to the definition that “R in N—R is bonded to the a ring, b ring and / or c ring by —O—, —S—, —C (—R) 2 — or a single bond”.
- This definition can be expressed by a compound having a ring structure represented by the following formula (2-3-1) in which X 1 and X 2 are incorporated into the condensed ring B ′ and the condensed ring C ′.
- a B ′ ring (or a ring formed by condensation of another ring so as to incorporate X 1 (or X 2 ) into the benzene ring which is the b ring (or c ring) in the general formula (2) (or C ′ ring).
- This compound is represented by, for example, compounds represented by the formulas (1-451) to (1-462) and formulas (1-1401) to (1-1460) listed as specific compounds described later.
- the condensed ring B ′ (or condensed ring C ′) formed corresponding to such a compound is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
- the above definition is a compound having a ring structure in which X 1 and / or X 2 is incorporated into the condensed ring A ′, which is represented by the following formula (2-3-2) or formula (2-3-3) But it can be expressed. That is, for example, a compound having an A ′ ring formed by condensing another ring so as to incorporate X 1 (and / or X 2 ) into the benzene ring which is the a ring in the general formula (2). .
- This compound corresponds to, for example, the compounds represented by formulas (1-471) to (1-479) listed as specific compounds described later, and the condensed ring A ′ formed is, for example, a phenoxazine ring. , A phenothiazine ring or an acridine ring.
- Examples of the “aryl ring” that is A ring, B ring and C ring in the general formula (1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, An aryl ring having 6 to 12 carbon atoms is more preferable, and an aryl ring having 6 to 10 carbon atoms is particularly preferable.
- the “aryl ring” is defined as “an aryl ring formed by bonding adjacent groups of R 1 to R 11 together with a ring, b ring or c ring” defined in the general formula (2).
- the total number of carbon atoms of the condensed ring in which a 5-membered ring is condensed is a carbon having a lower limit. Number.
- aryl rings include monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings, tricyclic terphenyl rings (m-terphenyl, o -Terphenyl, p-terphenyl), condensed tricyclic systems such as acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, condensed tetracyclic systems such as triphenylene ring, pyrene ring, naphthacene ring, condensed pentacyclic system Examples include a perylene ring and a pentacene ring.
- heteroaryl ring that is A ring, B ring and C ring in the general formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms.
- a heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is more preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable.
- heteroaryl ring include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as a ring constituent atom.
- the “heteroaryl ring” is a heteroaryl formed together with a ring, b ring or c ring by bonding adjacent groups of “R 1 to R 11 ” defined in the general formula (2).
- the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the condensed ring in which a 5-membered ring is condensed is lower limit. The number of carbons.
- heteroaryl ring examples include pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring Cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, p
- At least one hydrogen in the above “aryl ring” or “heteroaryl ring” is the first substituent, which is substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “Diarylamino”, substituted or unsubstituted “diheteroarylamino”, substituted or unsubstituted “arylheteroarylamino”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “alkoxy”, or substituted Alternatively, it may be substituted with an unsubstituted “aryloxy”, but as this first substituent, “aryl”, “heteroaryl”, “diarylamino” aryl, “diheteroarylamino” heteroaryl , “Arylheteroarylamino” aryl and heteroaryl, and “aryloxy” aryl It is a monovalent radical of the above-de
- the “alkyl” as the first substituent may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms. .
- Alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons) is preferable, alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons) is more preferable, and alkyl having 1 to 6 carbons.
- alkyl having 1 to 4 carbon atoms branched alkyl having 3 to 4 carbon atoms
- alkyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, and 1-methyl.
- Pentyl 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propyl Pentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n- Tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-hepta Sill, n- octadecyl, such as n- eicosyl, and the like
- examples of the “alkoxy” as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms.
- Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbons (branched alkoxy having 3 to 12 carbon atoms) is more preferred, and carbon number 1 More preferred are alkoxy having 6 to 6 (branched alkoxy having 3 to 6 carbon atoms), and particularly preferred are alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms).
- alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.
- the first substituent substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “diarylamino”, substituted or unsubstituted “diheteroarylamino”, substituted Or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl”, substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy” is described as substituted or unsubstituted As indicated, at least one hydrogen in them may be substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, and alkyl.
- aryl ring or “heteroaryl ring”, and the first substituent.
- alkyl as a substituent of
- at least one hydrogen thereof is substituted with an aryl such as phenyl (specific examples are described above) or an alkyl such as methyl (specific examples are described above). These are also included in the aryl or heteroaryl as the second substituent.
- the second substituent is a carbazolyl group
- a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl or an alkyl such as methyl is also used as the second substituent. Included in aryl.
- the aryl, heteroaryl, diarylamino aryl, diheteroarylamino heteroaryl, arylheteroarylamino aryl and heteroaryl, or aryloxy aryl in R 1 to R 11 in the general formula (2) may be represented by the general formula Examples thereof include the monovalent group of “aryl ring” or “heteroaryl ring” described in (1).
- the alkyl or alkoxy in R 1 to R 11 the description of “alkyl” or “alkoxy” as the first substituent in the description of the general formula (1) described above can be referred.
- aryl, heteroaryl or alkyl as a substituent for these groups is the same.
- R 1 to R 11 when adjacent groups of R 1 to R 11 are bonded to form an aryl ring or a heteroaryl ring together with a ring, b ring or c ring, it is a substituent to these rings.
- R in Si—R and Ge—R in Y 1 of the general formula (1) is aryl or alkyl, and examples of the aryl and alkyl include those described above.
- aryl having 6 to 10 carbon atoms for example, phenyl and naphthyl
- alkyl having 1 to 4 carbon atoms for example, methyl and ethyl
- R of N—R in X 1 and X 2 of the general formula (1) is aryl, heteroaryl or alkyl which may be substituted with the second substituent described above, and at least one hydrogen in aryl or heteroaryl May be substituted, for example, with alkyl.
- the aryl, heteroaryl and alkyl include those described above.
- aryl having 6 to 10 carbon atoms for example, phenyl, naphthyl and the like
- heteroaryl having 2 to 15 carbon atoms for example, carbazolyl and the like
- alkyl having 1 to 4 carbon atoms for example, methyl, ethyl and the like
- R in “—C (—R) 2 —” which is a linking group in the general formula (1) is hydrogen or alkyl, and examples of the alkyl include those described above. In particular, alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, etc.) is preferable. This explanation is the same for “—C (—R) 2 —” which is a linking group in the general formula (2).
- the present invention also provides a multimer of polycyclic aromatic compounds having a plurality of unit structures represented by the general formula (1), preferably a polycyclic aromatic having a plurality of unit structures represented by the general formula (2).
- the multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer.
- the multimer may be in a form having a plurality of the above unit structures in one compound.
- the unit structure is a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group.
- any ring (A ring, B ring or C ring, a ring, b ring or c ring) included in the unit structure is bonded so as to be shared by a plurality of unit structures
- any ring (A ring, B ring or C ring, a ring, b ring or c ring) included in the unit structure may be combined to be condensed. Good.
- Examples of such multimers include the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5). -4) or a multimeric compound represented by formula (2-6).
- the multimeric compound represented by the following formula (2-4) corresponds to, for example, a compound represented by the following formula (1-21). That is, if it explains by general formula (2), it is a multimeric compound which has the unit structure represented by several general formula (2) in one compound so that the benzene ring which is a ring may be shared.
- the multimeric compound represented by the following formula (2-4-1) corresponds to a compound represented by, for example, the formula (1-2665) described later.
- the general formula (2) is a multimeric compound having a unit structure represented by two general formulas (2) in one compound so as to share a benzene ring which is a ring.
- the multimeric compound represented by the following formula (2-4-2) corresponds to, for example, a compound represented by the following formula (1-2666).
- the general formula (2) is a multimeric compound having a unit structure represented by two general formulas (2) in one compound so as to share a benzene ring which is a ring.
- multimeric compounds represented by the following formulas (2-5-1) to (2-5-4) are represented by, for example, formulas (1-22) to (1-25) described later. Corresponds to the compound.
- a single compound has a plurality of unit structures represented by the general formula (2) so as to share the benzene ring which is the b ring (or c ring). It is a multimeric compound.
- the multimeric compound represented by the following formula (2-6) corresponds to, for example, compounds represented by formulas (1-31) to (1-37) described later.
- a benzene ring which is b ring (or a ring, c ring) of a certain unit structure and a benzene ring which is b ring (or a ring, c ring) of a certain unit structure Is a multimeric compound having a plurality of unit structures represented by the general formula (2) in one compound.
- the multimeric compound includes a multimerized form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), and formulas (2-5-1) to (2) -5-4) or a multimer in combination with a multimerized form represented by formula (2-6) may be used, and may be represented by formula (2-5-1) to formula (2-5) 4) may be a multimer in which the multimerized form represented by any one of 4) and the multimerized form represented by formula (2-6) are combined.
- Formula (2-4) and formula (2) -4-1) or the multimerized form represented by formula (2-4-2) and the multimerized form represented by any of formulas (2-5-1) to (2-5-4) A multimer combined with the multimerized form represented by the formula (2-6) may be used.
- all or a part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and the multimer thereof may be deuterium.
- all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and the multimer thereof may be halogen.
- a ring, B ring, C ring (A to C rings are aryl rings or heteroaryl rings), a substituent to the A to C rings, Y 1 is Si—R or Ge—R
- Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.
- the polycyclic aromatic compound and its multimer according to the present invention can be used as a material for organic devices.
- an organic device an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, etc. are mention
- Y 1 is B
- X 1 and X 2 are N—R compounds
- Y 1 is B
- X 1 is O
- X 2 is N—R.
- polycyclic aromatic compound and multimers thereof according to the present invention include, for example, compounds represented by the following formulas (1-1) to (1-825), and the following formulas (1-1001) to Compounds represented by (1-11281), compounds represented by the following formulas (1-1301) to (1-1131), compounds represented by the following formulas (1-11351) to (1-1361), and Examples thereof include compounds represented by the following formulas (1-11401) to (1-1460).
- polycyclic aromatic compound and multimers thereof include, for example, compounds represented by the following formulas (1-2001) to (1-2299), and the following formulas (1-2301) to Compounds represented by (1-2619), compounds represented by the following formulas (1-2621) to (1-2705), compounds represented by the following formulas (1-3581) to (1-3828), Compounds represented by formulas (1-3831) to (1-4033), compounds represented by formulas (1-4041) to (1-4288) below, and formulas (1-4301) to (1- 4349).
- the polycyclic aromatic compound and the multimer thereof according to the present invention include a phenyloxy group at the para position with respect to Y 1 in at least one of A ring, B ring and C ring (a ring, b ring and c ring),
- a carbazolyl group or a diphenylamino group By introducing a carbazolyl group or a diphenylamino group, an improvement in T1 energy (approximately 0.01 to 0.1 eV improvement) can be expected.
- a phenyloxy group is introduced at the para position with respect to B (boron), whereby A Since HOMO on the benzene ring which is a ring, B ring and C ring (a ring, b ring and c ring) is more localized at the meta position relative to boron, and LUMO is localized at the ortho and para positions relative to boron, An improvement in T1 energy can be particularly expected.
- R is alkyl, which may be linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms.
- Alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons) is preferable, alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons) is more preferable, and alkyl having 1 to 6 carbons.
- R include phenyl.
- “PhO—” is a phenyloxy group, and this phenyl may be substituted with a linear or branched alkyl such as, for example, formula (1-4421-1).
- alkyl having 1 to 18 carbon atoms branched alkyl having 3 to 18 carbon atoms
- alkyl having 1 to 12 carbon atoms 3 to 12 carbon atoms
- Branched chain alkyl alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). May be.
- polycyclic aromatic compound and multimers thereof include the above-described formulas (1-1) to (1-825), formulas (1-1001) to (1-11281), Formulas (1-1301) to (1-11311), Formulas (1-11351) to (1-1361), Formulas (1-1401) to (1-1460), Formulas (1-2001) to (1-2299) ), Formulas (1-2301) to (1-2619), formulas (1-2621) to (1-2705), formulas (1-3581) to (1-3828), formulas (1-3831) to (1 ⁇ 4033), formulas (1-4041) to (1-4288), formulas (1-4301) to (1-4349), formulas (1-4401) to (1-4422), and formulas (1-4501) ) To (1-4522), one or more aromatic rings in the compound Examples thereof include compounds in which at least one hydrogen atom is substituted with one or more alkyls or aryls, and more preferably 1 to 2 alkyls having 1 to 12 carbon atoms or aryls having
- each R is independently alkyl having 1 to 12 carbons or aryl having 6 to 10 carbons, preferably alkyl having 1 to 4 carbons or phenyl, and n is independently 0 to 2, Preferably it is 1.
- polycyclic aromatic compound and multimers thereof include one or more hydrogens in at least one phenyl group or one phenylene group in the compound.
- a compound substituted with is
- Examples of such compounds include compounds represented by the above formulas (1-1) to (1-825), compounds represented by the formulas (1-1001) to (1-11281), and formulas (1-1301).
- Compounds represented by (1-11311 compounds represented by formulas (1-11351) to (1-1361), compounds represented by formulas (1-1401) to (1-1460), 1-2001) to (1-2299), compounds represented by formulas (1-2301) to (1-2619), and formulas (1-2621) to (1-2705)
- the compounds containing a phenyl group or a phenylene group at least one hydrogen in the one or more phenyl groups or one phenylene group is alkyl having 1 to 4 carbon atoms, preferably one or more And a compound substituted with one to three alkyl groups (preferably one
- the polycyclic aromatic compounds represented by the general formulas (1) and (2) and multimers thereof are basically composed of A ring (a ring) and B An intermediate is produced by bonding a ring (ring b) and a ring C (ring c) with a linking group (a group containing X 1 and X 2 ) (first reaction), and then ring A (ring a) ), B ring (b ring) and C ring (c ring) can be combined with a linking group (a group containing Y 1 ) to produce the final product (second reaction).
- a general reaction such as a nucleophilic substitution reaction and an Ullmann reaction can be used for an etherification reaction, and a general reaction such as a Buchwald-Hartwig reaction can be used for an amination reaction.
- a tandem hetero Friedel-Crafts reaction continuous aromatic electrophilic substitution reaction, the same applies hereinafter
- the second reaction is a reaction for introducing Y 1 that connects the A ring (a ring), the B ring (b ring), and the C ring (c ring).
- Y 1 is a boron atom and X 1 and X 2 are oxygen atoms is shown below.
- a hydrogen atom and n- butyllithium between X 1 and X 2 ortho-metalated with sec- butyllithium or t- butyl lithium, and the like.
- Bronsted base such as N, N-diisopropylethylamine is added to cause tandem Bora Friedel-Crafts reaction. You can get things.
- a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.
- the said scheme (1) and (2) mainly show the manufacturing method of the polycyclic aromatic compound represented by General formula (1) or (2), about the multimer, about several It can manufacture by using the intermediate body which has A ring (a ring), B ring (b ring), and C ring (c ring). Details will be described in the following schemes (3) to (5).
- the target product can be obtained by setting the amount of the reagent such as butyl lithium to be doubled or tripled.
- lithium is introduced into a desired position by orthometalation.
- a bromine atom or the like is introduced at a position where lithium is to be introduced, and halogen-metal exchange is also performed.
- Lithium can be introduced at the desired location.
- a halogen such as a bromine atom or a chlorine atom is introduced at a position where lithium is to be introduced as in the above schemes (6) and (7).
- Lithium can be introduced into a desired position also by exchange (the following schemes (8), (9) and (10)).
- This method is useful because the target product can be synthesized even in the case where ortho-metalation is not possible due to the influence of substituents.
- Y 1 is a boron atom and X 1 and X 2 are nitrogen atoms is shown in the following schemes (11) and (12).
- X 1 and X 2 are oxygen atoms
- the hydrogen atom between X 1 and X 2 is first ortho-metalated with n-butyllithium or the like.
- boron tribromide and the like are added, and after lithium-boron metal exchange is performed, Brensted base such as N, N-diisopropylethylamine is added to cause tandem Bora Friedel-Crafts reaction to obtain the target product.
- a Lewis acid such as aluminum trichloride may be added to promote the reaction.
- a halogen such as a bromine atom or a chlorine atom is introduced at the position where lithium is to be introduced as in the above schemes (6) and (7).
- lithium can be introduced into the desired position also by halogen-metal exchange (Schemes (13), (14) and (15) below).
- m-CPBA m-chloroperbenzoic acid
- a halogen such as a bromine atom or a chlorine atom is located at a position where lithium is to be introduced as in the above schemes (6) and (7). And lithium can be introduced into a desired position also by halogen-metal exchange (the following schemes (20), (21) and (22)).
- the thus-produced multimer in which Y 1 is a phosphorous sulfide and X 1 and X 2 are oxygen atoms is also represented by m-chloroperbenzoic acid (in the above schemes (18) and (19)).
- a compound in which Y 1 is a phosphorus oxide can be obtained by treatment with m-CPBA), and a compound in which Y 1 is a phosphorus atom can be obtained by treatment with triethylphosphine.
- Y 1 is B, P, P ⁇ O or P ⁇ S, and X 1 and X 2 are O or NR is described.
- Y 1 is A compound in which Al, Ga, As, Si—R or Ge—R, or X 1 and X 2 are S can also be synthesized.
- solvent used in the above reaction examples include t-butylbenzene and xylene.
- the polycyclic aromatic compound represented by the general formula (2) has the formula (2-) in the following schemes (23) and (24) depending on the mutual bonding form of the substituents in the a-ring, b-ring and c-ring. As shown in 1) and formula (2-2), the ring structure constituting the compound changes. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following schemes (23) and (24).
- the A ′ ring, the B ′ ring and the C ′ ring are formed by bonding adjacent groups of the substituents R 1 to R 11 to each of a An aryl ring or a heteroaryl ring formed together with a ring, b ring and c ring is shown (also referred to as a condensed ring formed by condensing another ring structure to the a ring, b ring or c ring).
- a multimeric compound is synthesized by using an orthometalation reagent such as butyl lithium in a molar amount twice or three times that of the intermediate 1. can do. Further, by introducing a halogen such as a bromine atom or a chlorine atom in advance at a position where a metal such as lithium is to be introduced, and replacing the halogen-metal, the metal can be introduced at a desired position.
- an orthometalation reagent such as butyl lithium in a molar amount twice or three times that of the intermediate 1.
- the orthometalation reagents used in the above schemes (1) to (27) include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, lithium diisopropylamide, and lithium tetramethyl.
- alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, lithium diisopropylamide, and lithium tetramethyl.
- Examples include organic alkali compounds such as piperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.
- the metal exchange reagent for metal-Y 1 used in the above schemes (1) to (27) includes Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 triiodide.
- halides of Y 1 such as halide, CIPN (NEt 2) 2 amination halide Y 1, such as, alkoxides of Y 1, an aryloxy compound of Y 1 are mentioned.
- the Bronsted base used in the above schemes (1) to (27) includes N, N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6. -Pentamethylpiperidine, N, N-dimethylaniline, N, N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar 4 BNa, Ar 4 BK, Ar 3 B, Ar 4 Si (where Ar is an aryl such as phenyl) and the like.
- a Bronsted base or a Lewis acid may be used to promote the tandem heterofriedel crafts reaction.
- Y 1 halides such as Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 triiodide
- an acid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, or hydrogen iodide is generated, it is effective to use a Bronsted base that captures the acid.
- the polycyclic aromatic compounds and multimers thereof of the present invention include those in which at least some of the hydrogen atoms are substituted with deuterium and those substituted with halogen such as fluorine or chlorine.
- halogen such as fluorine or chlorine.
- Such a compound can be synthesized in the same manner as described above by using a raw material in which a desired portion is deuterated, fluorinated or chlorinated.
- the polycyclic aromatic compound and multimer thereof according to the present invention can be used as a material for organic devices.
- an organic device an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, etc. are mention
- FIG. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.
- An organic electroluminescent device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103.
- the cathode 108 provided on the electron injection layer 107.
- the organic electroluminescent element 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer.
- a structure including the hole injection layer 103 provided above and the anode 102 provided on the hole injection layer 103 may be employed.
- each said layer may consist of a single layer, respectively, and may consist of multiple layers.
- the substrate 101 serves as a support for the organic electroluminescent device 100, and usually quartz, glass, metal, plastic, or the like is used.
- the substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose.
- a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used.
- glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone and the like are preferable.
- soda lime glass, non-alkali glass, or the like is used, and the thickness only needs to be sufficient to maintain the mechanical strength.
- the upper limit value of the thickness is, for example, 2 mm or less, preferably 1 mm or less.
- the glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass.
- soda lime glass with a barrier coat such as SiO 2 is also commercially available, so it can be used. it can.
- the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one surface in order to improve the gas barrier property, and a synthetic resin plate, film or sheet having a low gas barrier property is used as the substrate 101. When used, it is preferable to provide a gas barrier film.
- the anode 102 serves to inject holes into the light emitting layer 105.
- the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .
- Examples of the material for forming the anode 102 include inorganic compounds and organic compounds.
- Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide) Products (IZO), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, and the like.
- Examples of the organic compound include polythiophene such as poly (3-methylthiophene), conductive polymer such as polypyrrole and polyaniline, and the like. In addition, it can select suitably from the substances currently used as an anode of an organic electroluminescent element, and can use it.
- the resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but is preferably low resistance from the viewpoint of power consumption of the light emitting element.
- an ITO substrate of 300 ⁇ / ⁇ or less functions as an element electrode, but at present, since it is possible to supply a substrate of about 10 ⁇ / ⁇ , for example, 100 to 5 ⁇ / ⁇ , preferably 50 to 5 ⁇ . It is particularly desirable to use a low resistance product of / ⁇ .
- the thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 50 to 300 nm.
- the hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104.
- the hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105.
- the hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one kind or two or more kinds of hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder. Is done.
- an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.
- a hole injection / transport material As a hole injection / transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. The hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do. For this purpose, it is preferable to use a substance that has a low ionization potential, a high hole mobility, excellent stability, and is less likely to generate trapping impurities during production and use.
- a polycyclic aromatic compound represented by the general formula (1) or a multimer thereof can be used as a material for forming the hole injection layer 103 and the hole transport layer 104.
- photoconductive materials compounds conventionally used as hole charge transport materials, p-type semiconductors, and known materials used in hole injection layers and hole transport layers of organic electroluminescence devices Any one can be selected and used. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), triarylamine derivatives (aromatic tertiary class).
- polycarbonates, styrene derivatives, polyvinylcarbazole, polysilanes, etc. having the aforementioned monomers in the side chain are preferred, but light emission There is no particular limitation as long as it is a compound that can form a thin film necessary for manufacturing the device, inject holes from the anode, and further transport holes.
- organic semiconductors are strongly influenced by the doping.
- Such an organic semiconductor matrix material is composed of a compound having a good electron donating property or a compound having a good electron accepting property.
- Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping of electron donor materials.
- TCNQ tetracyanoquinone dimethane
- F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane
- the light emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied.
- the material for forming the light-emitting layer 105 may be a compound that emits light by being excited by recombination of holes and electrons (a light-emitting compound), can form a stable thin film shape, and is in a solid state It is preferable that the compound exhibits a strong light emission (fluorescence) efficiency.
- the polycyclic aromatic compound represented by the general formula (1) or a multimer thereof can be used as the material for the light emitting layer.
- the light emitting layer may be either a single layer or a plurality of layers, each formed of a light emitting layer material (host material, dopant material).
- a light emitting layer material host material, dopant material
- Each of the host material and the dopant material may be one kind or a plurality of combinations.
- the dopant material may be included in the host material as a whole, or may be included partially.
- As a doping method it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited.
- the amount of host material used depends on the type of host material and can be determined according to the characteristics of the host material.
- the standard of the amount of the host material used is preferably 50 to 99.999% by weight of the entire light emitting layer material, more preferably 80 to 99.95% by weight, and still more preferably 90 to 99.9% by weight. It is.
- the polycyclic aromatic compound represented by the general formula (1) or a multimer thereof can also be used as a host material.
- the amount of dopant material used depends on the type of dopant material, and can be determined according to the characteristics of the dopant material.
- the standard of the amount of dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and further preferably 0.1 to 10% by weight of the entire material for the light emitting layer. is there.
- the above range is preferable in that, for example, the concentration quenching phenomenon can be prevented.
- the polycyclic aromatic compound represented by the general formula (1) or a multimer thereof can also be used as a dopant material.
- Examples of the host material that can be used in combination with the polycyclic aromatic compound represented by the general formula (1) or a multimer thereof include fused ring derivatives such as anthracene and pyrene, which have been known as light emitters, and bisstyryl. Examples thereof include bisstyryl derivatives such as anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.
- dopant material which can be used together with the polycyclic aromatic compound represented by the said General formula (1), or its multimer, A well-known compound can be used and desired. Depending on the emission color, various materials can be selected.
- condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazoles Derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, distyrylbenzene derivatives, etc.
- condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pent
- blue to blue-green dopant materials include naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, chrysene and other aromatic hydrocarbon compounds and derivatives thereof, furan, pyrrole, thiophene, Aromatic complex such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene Ring compounds and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazo
- green to yellow dopant material examples include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene.
- a compound in which a substituent capable of increasing the wavelength such as aryl, heteroaryl, arylvinyl, amino, cyano is introduced into the compound exemplified as a blue-green dopant material is also a suitable example.
- orange to red dopant materials include naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone Derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazo Derivatives, thi
- the dopant can be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13, and references cited therein.
- amines having a stilbene structure perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives or pyrene derivatives are particularly preferable.
- the amine having a stilbene structure is represented by the following formula, for example.
- Ar 1 is an m-valent group derived from aryl having 6 to 30 carbon atoms
- Ar 2 and Ar 3 are each independently aryl having 6 to 30 carbon atoms
- Ar 1 to Ar At least one of 3 has a stilbene structure
- Ar 1 to Ar 3 may be substituted
- m is an integer of 1 to 4.
- the amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula.
- Ar 2 and Ar 3 are each independently aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted.
- aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, stilbene, distyrylbenzene, distyrylbiphenyl, and distyryl.
- fluorene include fluorene.
- amines having a stilbene structure include N, N, N ′, N′-tetra (4-biphenylyl) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (1-naphthyl) ) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (2-naphthyl) -4,4′-diaminostilbene, N, N′-di (2-naphthyl) -N, N '-Diphenyl-4,4'-diaminostilbene, N, N'-di (9-phenanthryl) -N, N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis [4 "-bis (Diphenylamino) styryl] -biphenyl, 1,4-bis [4′-bis (diphenylamino)
- perylene derivatives examples include 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, 3,10-diphenylperylene, 3,4- Diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) -8,11-di (t-butyl) perylene 3- (9′-anthryl) -8,11-di (t-butyl) perylene, 3,3′-bis (8,11-di (t-butyl) perylenyl), and the like.
- JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, Perylene derivatives described in JP-A No. 2000-34234, JP-A No. 2001-267075, JP-A No. 2001-217077 and the like may be used.
- borane derivatives examples include 1,8-diphenyl-10- (dimesitylboryl) anthracene, 9-phenyl-10- (dimesitylboryl) anthracene, 4- (9′-anthryl) dimesitylborylnaphthalene, 4- (10 ′ -Phenyl-9'-anthryl) dimesitylborylnaphthalene, 9- (dimesitylboryl) anthracene, 9- (4'-biphenylyl) -10- (dimesitylboryl) anthracene, 9- (4 '-(N-carbazolyl) phenyl) And -10- (dimesitylboryl) anthracene.
- the aromatic amine derivative is represented by the following formula, for example.
- Ar 4 is an n-valent group derived from aryl having 6 to 30 carbon atoms
- Ar 5 and Ar 6 are each independently aryl having 6 to 30 carbon atoms
- Ar 4 to Ar 6 are It may be substituted and n is an integer from 1 to 4.
- Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene
- Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms
- Ar 4 to Ar 6 Are more preferably aromatic amine derivatives wherein n is 2 and n is 2.
- aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorenephenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, pentacene and the like.
- the chrysene type includes, for example, N, N, N ′, N′-tetraphenylchrysene-6,12-diamine, N, N, N ′, N′-tetra (p-tolyl) Chrysene-6,12-diamine, N, N, N ′, N′-tetra (m-tolyl) chrysene-6,12-diamine, N, N, N ′, N′-tetrakis (4-isopropylphenyl) chrysene -6,12-diamine, N, N, N ', N'-tetra (naphthalen-2-yl) chrysene-6,12-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) ) Chrysene-6,12-diamine, N, N′-diphenyl-N, N′-bis (4
- Examples of the pyrene series include N, N, N ′, N′-tetraphenylpyrene-1,6-diamine, N, N, N ′, N′-tetra (p-tolyl) pyrene-1,6.
- anthracene system examples include N, N, N, N-tetraphenylanthracene-9,10-diamine, N, N, N ′, N′-tetra (p-tolyl) anthracene-9,10-diamine.
- Examples of coumarin derivatives include coumarin-6 and coumarin-334. Moreover, you may use the coumarin derivative described in Unexamined-Japanese-Patent No. 2004-43646, Unexamined-Japanese-Patent No. 2001-76876, and Unexamined-Japanese-Patent No. 6-298758.
- Examples of the pyran derivative include the following DCM and DCJTB. Also, JP 2005-126399, JP 2005-097283, JP 2002-234892, JP 2001-220577, JP 2001-081090, and JP 2001-052869. Alternatively, pyran derivatives described in the above may be used.
- the electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106.
- the electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105.
- the electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more electron transport / injection materials or a mixture of the electron transport / injection material and the polymer binder.
- the electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and further transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is preferable to use a substance that has a high electron affinity, a high electron mobility, excellent stability, and is unlikely to generate trapping impurities during production and use. However, considering the transport balance between holes and electrons, if the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination is mainly played, the electron transport capability is much higher. Even if it is not high, the effect of improving the luminous efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron injection / transport layer in this embodiment may include a function of a layer that can efficiently block the movement of holes.
- a material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 a polycyclic aromatic compound represented by the general formula (1) or a multimer thereof can be used.
- it can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in electron injection layers and electron transport layers of organic electroluminescent devices. .
- Materials used for the electron transport layer or the electron injection layer include compounds composed of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, and pyrrole derivatives. And at least one selected from the condensed ring derivatives thereof and metal complexes having electron-accepting nitrogen.
- condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinones And quinone derivatives such as diphenoquinone, phosphorus oxide derivatives, carbazole derivatives, and indole derivatives.
- metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.
- electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazoles.
- metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. can give.
- the above-mentioned materials can be used alone, but they may be mixed with different materials.
- quinolinol metal complexes Among the materials described above, quinolinol metal complexes, bipyridine derivatives, phenanthroline derivatives or borane derivatives are preferred.
- the quinolinol-based metal complex is a compound represented by the following general formula (E-1).
- R 1 to R 6 are hydrogen or a substituent
- M is Li, Al, Ga, Be or Zn
- n is an integer of 1 to 3.
- quinolinol metal complexes include 8-quinolinol lithium, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris (3 , 4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) ( Phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolato) aluminum, bis (2-methyl-8- Quinolinolato) (4- Tylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolate)
- the bipyridine derivative is a compound represented by the following general formula (E-2).
- G represents a simple bond or an n-valent linking group, and n is an integer of 2 to 8. Further, carbon not used for bonding of pyridine-pyridine or pyridine-G may be substituted.
- G in the general formula (E-2) examples include the following structural formulas.
- each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl.
- pyridine derivative examples include 2,5-bis (2,2′-pyridin-6-yl) -1,1-dimethyl-3,4-diphenylsilole, 2,5-bis (2,2′- Pyridin-6-yl) -1,1-dimethyl-3,4-dimesitylsilole, 2,5-bis (2,2′-pyridin-5-yl) -1,1-dimethyl-3,4 Diphenylsilole, 2,5-bis (2,2′-pyridin-5-yl) -1,1-dimethyl-3,4-dimesitylsilole, 9,10-di (2,2′-pyridine-6) -Yl) anthracene, 9,10-di (2,2′-pyridin-5-yl) anthracene, 9,10-di (2,3′-pyridin-6-yl) anthracene, 9,10-di (2 , 3′-Pyridin-5-yl)
- the phenanthroline derivative is a compound represented by the following general formula (E-3-1) or (E-3-2).
- R 1 to R 8 are hydrogen or a substituent, adjacent groups may be bonded to each other to form a condensed ring, G represents a simple bond or an n-valent linking group, and n represents 2 It is an integer of ⁇ 8.
- Examples of G in the general formula (E-3-2) include the same ones as described in the bipyridine derivative column.
- phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-phenanthroline- 2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9′-difluor -Bis (1,10-phenanthroline-5-yl), bathocuproin, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene and the like.
- a phenanthroline derivative is used for the electron transport layer and the electron injection layer.
- the substituent itself has a three-dimensional structure, or a phenanthroline skeleton or Those having a three-dimensional structure by steric repulsion with an adjacent substituent or those having a plurality of phenanthroline skeletons linked to each other are preferred.
- a compound containing a conjugated bond, a substituted or unsubstituted aromatic hydrocarbon, or a substituted or unsubstituted aromatic heterocycle in the linking unit is more preferable.
- the borane derivative is a compound represented by the following general formula (E-4), and is disclosed in detail in JP-A-2007-27587.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- R 13 to R 16 are each independently an optionally substituted alkyl or an optionally substituted aryl
- X is an optionally substituted arylene
- Y is Optionally substituted aryl having 16 or less carbon atoms, substituted boryl, or optionally substituted carbazolyl
- n is each independently an integer of 0 to 3.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- R 13 to R 16 are each independently an optionally substituted alkyl or an optionally substituted aryl
- R 21 and R 22 are each independently hydrogen, alkyl, At least one of optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocyclic ring, or cyano
- X 1 is optionally substituted arylene having 20 or less carbon atoms.
- N is each independently an integer from 0 to 3
- m is each independently an integer from 0 to 4.
- R 31 to R 34 are each independently methyl, isopropyl or phenyl
- R 35 and R 36 are each independently hydrogen, methyl, isopropyl or phenyl. It is.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- Each of R 13 to R 16 independently represents an optionally substituted alkyl or an optionally substituted aryl, and X 1 represents an optionally substituted arylene having 20 or less carbon atoms.
- n is each independently an integer of 0 to 3.
- R 31 to R 34 are each independently any of methyl, isopropyl or phenyl
- R 35 and R 36 are each independently any of hydrogen, methyl, isopropyl or phenyl It is.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- Each of R 13 to R 16 independently represents an optionally substituted alkyl or an optionally substituted aryl, and X 1 represents an optionally substituted arylene having 10 or less carbon atoms.
- Y 1 is optionally substituted aryl having 14 or less carbon atoms, and n is each independently an integer of 0 to 3.
- R 31 to R 34 are each independently methyl, isopropyl or phenyl
- R 35 and R 36 are each independently hydrogen, methyl, isopropyl or phenyl. It is.
- the benzimidazole derivative is a compound represented by the following general formula (E-5).
- Ar 1 to Ar 3 are each independently hydrogen or aryl having 6 to 30 carbon atoms which may be substituted.
- a benzimidazole derivative which is anthryl optionally substituted with Ar 1 is preferable.
- aryl having 6 to 30 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, acenaphthylene-1-yl, acenaphthylene-3-yl, acenaphthylene-4-yl, acenaphthylene-5-yl, and fluorene-1- Yl, fluoren-2-yl, fluoren-3-yl, fluoren-4-yl, fluoren-9-yl, phenalen-1-yl, phenalen-2-yl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-anthryl, 2-anthryl, 9-anthryl, fluoranthen-1-yl, fluoranthen-2-yl, fluoranthen-3-yl, fluoranthen-7-yl, fluoranthen-8-yl, Triphenylene-1-yl, 2-
- benzimidazole derivative examples include 1-phenyl-2- (4- (10-phenylanthracen-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (naphthalene-2) -Yl) anthracen-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -1- Phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalen-2-yl) anthracen-9-yl) -1,2-diphenyl-1H-benzo [d] imidazole, 1- (4- (10 -(Naphthalen-2-yl) anthracen-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (n)-
- the electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer.
- a substance capable of reducing the material forming the electron transport layer or the electron injection layer various substances can be used as long as they have a certain reducing ability.
- Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2. 9eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and alkaline earth metals such as those having a work function of 2.9 eV or less are particularly preferable.
- a more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs.
- alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL element can be improved and the lifetime can be extended.
- a reducing substance having a work function of 2.9 eV or less a combination of two or more alkali metals is also preferable.
- a combination containing Cs such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
- Cs such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
- the cathode 108 serves to inject electrons into the light emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.
- the material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as that for forming the anode 102 can be used.
- metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or alloys thereof (magnesium-silver alloy, magnesium -Indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum, etc.) are preferred.
- Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics.
- metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example.
- the method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.
- the materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, Polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin It can also be used by dispersing it in solvent-soluble resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, etc. is there.
- solvent-soluble resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins,
- Each layer constituting the organic electroluminescent element is formed by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method or cast method, coating method, etc. It can be formed by using a thin film.
- the film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like.
- the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, and the like.
- Deposition conditions generally include boat heating temperature +50 to + 400 ° C., vacuum degree 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / second, substrate temperature ⁇ 150 to + 300 ° C., film thickness 2 nm to 5 ⁇ m. It is preferable to set appropriately within the range.
- an organic electric field composed of an anode / hole injection layer / hole transport layer / a light emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode.
- a method for manufacturing a light-emitting element will be described.
- a thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode.
- a host material and a dopant material are co-evaporated to form a thin film to form a light emitting layer.
- An electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by vapor deposition. By forming it as a cathode, a desired organic electroluminescent element can be obtained.
- the order of preparation may be reversed, and the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode may be fabricated in this order. Is possible.
- the anode When a DC voltage is applied to the organic electroluminescent device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, the organic electroluminescent device is transparent or translucent. Luminescence can be observed from the electrode side (anode or cathode, and both). The organic electroluminescence device emits light when a pulse current or an alternating current is applied. The alternating current waveform to be applied may be arbitrary.
- the present invention can also be applied to a display device provided with an organic electroluminescent element or a lighting device provided with an organic electroluminescent element.
- a display device or an illuminating device including an organic electroluminescent element can be manufactured by a known method such as connecting the organic electroluminescent element according to the present embodiment and a known driving device, such as direct current driving, pulse driving, or alternating current. It can be driven by appropriately using a known driving method such as driving.
- Examples of the display device include a panel display such as a color flat panel display, and a flexible display such as a flexible color organic electroluminescence (EL) display (for example, JP-A-10-335066 and JP-A-2003-321546). Gazette, JP-A-2004-281086, etc.).
- Examples of the display method of the display include a matrix and / or segment method. Note that the matrix display and the segment display may coexist in the same panel.
- a matrix is a pixel in which pixels for display are arranged two-dimensionally, such as a grid or mosaic, and displays characters and images as a set of pixels.
- the shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 ⁇ m or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become.
- monochrome display pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type.
- the matrix driving method may be either a line sequential driving method or an active matrix.
- the line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
- a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light.
- a predetermined region is caused to emit light.
- the time and temperature display in a digital clock or a thermometer the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned.
- the illuminating device examples include an illuminating device such as indoor lighting, a backlight of a liquid crystal display device, and the like (for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A).
- the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like.
- a backlight for liquid crystal display devices especially personal computers for which thinning is an issue, considering that conventional methods are made of fluorescent lamps and light guide plates, it is difficult to reduce the thickness.
- the backlight using the light emitting element according to the embodiment is thin and lightweight.
- polycyclic aromatic compound and the multimer thereof according to the present invention can be used for producing an organic field effect transistor or an organic thin film solar cell in addition to the organic electroluminescent element described above.
- An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and includes a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the current can be controlled by arbitrarily blocking the flow of electrons (or holes) flowing between the source electrode and the drain electrode.
- Field effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.
- the structure of the organic field effect transistor is usually provided with a source electrode and a drain electrode in contact with an organic semiconductor active layer formed by using the polycyclic aromatic compound according to the present invention and a multimer thereof, and further an organic semiconductor
- the gate electrode only needs to be provided with an insulating layer (dielectric layer) in contact with the active layer interposed therebetween.
- Examples of the element structure include the following structures.
- Substrate / gate electrode / insulator layer / source electrode / drain electrode / organic semiconductor active layer (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode / drain electrode (3) substrate / organic Semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode It can be applied as a pixel drive switching element of an active matrix drive type liquid crystal display or an organic electroluminescence display.
- Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass.
- the photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side.
- the polycyclic aromatic compound and its multimer according to the present invention can be used as materials for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on the physical properties.
- the polycyclic aromatic compound and the multimer thereof according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell.
- the organic thin film solar cell may appropriately include a hole block layer, an electron block layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like.
- known materials used for the organic thin film solar cell can be appropriately selected and used in combination.
- a 1.6M n-butyllithium hexane solution (0.75 ml) was added to a flask containing diphenoxybenzene (0.26 g) and ortho-xylene (3.0 ml) at 0 ° C. under a nitrogen atmosphere. . After stirring for 30 minutes, the temperature was raised to 70 ° C., and the mixture was further stirred for 4 hours. Hexane was distilled off by heating and stirring at 100 ° C. under a nitrogen stream, and then cooled to ⁇ 20 ° C., boron tribromide (0.114 ml) was added, and the mixture was stirred for 1 hour.
- N, N-diisopropylethylamine 0.342 ml was added and the mixture was heated and stirred at 120 ° C. for 5 hours. Thereafter, N, N-diisopropylethylamine (0.171 ml) was added, followed by filtration using a Florisil short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with methanol to obtain a compound (0.121 g) represented by the formula (1-1) as a white solid.
- the filtrate was separated, and the solvent of the organic layer was distilled off under reduced pressure. Then, the filtrate was dissolved in ethyl acetate and reprecipitated by adding heptane. Further, the mixture was passed through a silica gel short path column (developing solution: heated chlorobenzene), the solvent was distilled off under reduced pressure, and the resulting solid was reprecipitated with ethyl acetate / heptane to give 1,3-bis ([1,1′-biphenyl]. ] -4-yloxy) benzene (33.0 g) was obtained.
- Synthesis example (6) Synthesis of N 6 , N 6 , N 8 , N 8 -tetraphenyl-5,9-dioxa-13b-boranaft [3,2,1-de] anthracene-6,8-diamine ((4,6-dibromo-1,3-phenylene) bis (oxy)) dibenzene (45.0 g), diphenylamine (45.0 g), Pd (dba) 2 (1.2 g), (4- (N, A flask containing N-dimethylamino) phenyl) di-tbutylphosphine (A- ta Phos) (1.1 g), NaOtBu (25.7 g) and toluene (250 ml) was heated to 100 ° C.
- N 1 , N 1 , N 3 , N 3 , N 5 , N 5 -hexaphenylbenzene-1,3,5-triamine (11.6 g, 20 mmol) and orthodichlorobenzene (ODCB, 120 mL) were added to nitrogen.
- ODCB orthodichlorobenzene
- boron tribromide (3.78 mL, 40 mmol) was added at room temperature, followed by heating and stirring at 170 ° C. for 48 hours. Thereafter, the reaction solution was distilled off under reduced pressure at 60 ° C. Filtration was performed using a Florisil short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with hexane to obtain a compound represented by the formula (1-447) as a yellow solid (11.0 g, yield 94%).
- Flask containing 2-bromo-1,3-difluorobenzene (12.0 g), [1,1′-biphenyl] -3-ol (23.0 g), potassium carbonate (34.0 g) and NMP (130 ml) was stirred for 10 hours at 170 ° C. under a nitrogen atmosphere. After the reaction was stopped, the reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
- 1,5-dibromo-2,4-difluorobenzene (30.0 g), phenylboronic acid (29.6 g), Pd (PPh 3 ) 4 (2.6 g), tripotassium phosphate (51. 0 g), toluene (400 ml), isopropanol (100 ml) and water (50 ml) were heated and stirred at reflux temperature for 5 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation.
- the solid obtained by distilling off the solvent under reduced pressure was washed with chlorobenzene. Further, it was dissolved in chlorobenzene and reprecipitated by adding ethyl acetate and ethanol to obtain 4 ′-(9H-carbazol-9-yl)-[1,1′-biphenyl] -4-ol (29.3 g). It was.
- the obtained crude product was dissolved in toluene, and the solid precipitated by adding heptane was filtered off, and the filtrate was purified by silica gel column chromatography (developing solution: toluene / heptane mixed solvent).
- the target product was eluted by gradually increasing the ratio of toluene in the developing solution, and further washed with ethyl acetate to obtain the compound (4.7 g) represented by the formula (1-1252).
- 1.6 M tert-butyllithium pentane solution 37.5 ml was added at ⁇ 30 ° C. under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was heated to 60 ° C. and stirred for 1 hour, and then components having a lower boiling point than tert-butylbenzene were distilled off under reduced pressure.
- N 1 , N 1 ′ -(1,3-phenylene) bis (2-chloro-N 1 , N 3 , N 3 -triphenylbenzene- is purified by activated carbon column chromatography (developing solution: toluene). 1,3-diamine) (22.0 g) was obtained.
- Flask containing 1,4-dibromo-2,3,5,6-tetrafluorobenzene (6.24 g), phenol (9.53 g), potassium carbonate (14.0 g) and NMP (20 ml) under nitrogen atmosphere was heated and stirred at 140 ° C. for 18 hours.
- the reaction solution was cooled to room temperature, and saturated brine and toluene were added to separate the layers.
- the residue was purified with a silica gel short pass column (developing solution: toluene).
- the solvent was distilled off under reduced pressure, and the crude product was washed with methanol to obtain 1,4-dibromo-2,3,5,6-tetraphenoxybenzene (9.64 g).
- 1.6M n-butyl was added to a solution of 1,4-dibromo-2,3,5,6-tetraphenoxybenzene (0.604 g) in t-butylbenzene (3.0 ml) at 0 ° C. in a nitrogen atmosphere. Lithium hexane solution (0.610 ml) was added. After stirring for 1 hour, the temperature was raised to room temperature, and t-butylbenzene (4.0 ml) was added. After cooling to ⁇ 50 ° C., boron tribromide (0.105 ml) was added and stirred for 30 minutes. After heating up to 0 degreeC and stirring for 30 minutes, it heated up to 60 degreeC and stirred for 10 hours.
- N, N-diisopropylethylamine (65.9 ⁇ l) was added, and the mixture was heated and stirred at reflux temperature for 11 hours.
- the reaction solution was cooled to room temperature, suction filtered through a glass filter covered with celite, and the solvent was distilled off under reduced pressure to obtain a crude product.
- the compound represented by the formula (1-21) (4.10 mg) was obtained as an orange solid.
- Resorcinol (14.4 g, 14.4 mmol), potassium carbonate (3.97 g, 28.7 mmol) and NMP (57.4 mL) were added to 2-bromo-1-fluoro-3-phenoxybenzene (57.4 mL) at room temperature under a nitrogen atmosphere. 7.67 g, 28.7 mmol) was added, and the mixture was heated and stirred at 150 ° C. for 160 hours, and then heated and stirred at 160 ° C. for 22 hours. Thereafter, NMP was distilled off under reduced pressure, and toluene was added. Filtration was performed using a Florisil short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product. Recrystallization from toluene gave 1,3-bis (2-bromo-3-phenoxyphenoxy) benzene as a white solid (5.35 g, yield 62%).
- N, N-diisopropylethylamine (0.348 mL, 2.0 mmol) was added at 0 ° C., and the mixture was stirred with heating at 150 ° C. for 20 hours, followed by filtration using a Florisil short pass column, and the solvent was distilled off under reduced pressure. The product was obtained. A white solid was obtained by washing with dichloromethane and acetonitrile. Subsequently, recrystallization was performed using ethyl acetate to obtain a compound represented by the formula (1-24) as a white solid (19.2 mg, yield: 8.3%).
- the filtrate was suction filtered using a glass filter, and the solvent of the filtrate was distilled off under reduced pressure, dissolved in toluene and suction filtered using a glass filter covered with silica gel, and then the solvent of the filtrate was distilled off under reduced pressure.
- the dichloromethane layer was separated, the aqueous layer was extracted with dichloromethane, the solvent was distilled off under reduced pressure, and the crude product was washed with hexane, methanol, acetonitrile, and ethyl acetate as a white solid.
- a compound (0.723 g) represented by the formula (1-1250) was obtained.
- the insoluble material was removed by filtration, the dichloromethane layer was separated, and the aqueous layer was extracted with dichloromethane.
- the obtained organic layers were combined and concentrated, followed by silica gel short pass column using dichloromethane and ethyl acetate as developing solvents, and the solvent of the filtrate was distilled off under reduced pressure.
- the obtained crude product was washed with methanol to obtain a compound (0.580 g) represented by the formula (1-1190) as a white solid.
- reaction solution was added to a solution of 1,4-diazabicyclo [2.2.2] octane (31.4 g, 280 mmol) in dichloromethane (300 ml), and then using a glass filter covered with celite. Then, the filtrate was concentrated under reduced pressure, diluted with toluene, and insoluble matter was removed by filtration.After the solvent of the filtrate was distilled off under reduced pressure, it was purified with a silica gel short path column (developing solution: dichloromethane).
- the insoluble material was removed by filtration, the dichloromethane layer was separated, and the aqueous layer was extracted with dichloromethane.
- the obtained crude product was washed with methanol to obtain a compound (1.04 g) represented by the formula (1-1191) as a white solid.
- N-diphenyl- [1,1′-biphenyl] -4-amine 7.2 g
- xylene 72 ml
- 6M n-butyllithium hexane solution 9.8 ml
- the mixture was heated to 70 ° C. and stirred for 3 hours, and components having a lower boiling point than xylene were distilled off under reduced pressure.
- boron tribromide 1.6 ml was added, and the mixture was warmed to room temperature and stirred for 30 minutes.
- Flask containing 5,9-dioxa-13b-thiophosphanaphtho [3,2,1-de] anthracene (3.5 g), N-bromosuccinimide (7.7 g) and DMF (60 ml) under nitrogen atmosphere was stirred at room temperature for 3 hours. After cooling the reaction solution to room temperature, water was added to dissolve the salt, and the target product was collected by suction filtration.
- 1.6M t-butyllithium pentane solution (45.3 ml) was added while cooling in an ice bath under a nitrogen atmosphere. After completion of the dropwise addition, the temperature was raised to 60 ° C. and stirred for 2 hours, and then components having a lower boiling point than t-butylbenzene were distilled off under reduced pressure.
- N 1 , N 1 , N 3 -triphenylbenzene-1,3-diamine (20.0 g), 1-bromo-2,3-dichlorobenzene (6.4 g), Pd-132 (0. 2 g), NaOtBu (6.8 g) and xylene (70 ml) were heated and stirred at 120 ° C. for 2 hours. After cooling the reaction solution to room temperature, water and ethyl acetate were added to separate the layers.
- N 1 , N 1 ′ -(2-chloro-1,3-phenylene) bis (N 1 , N 3 , N 3 -triphenylbenzene-1,3-diamine) (12.0 g) and t-butylbenzene (
- 1.7 M t-butyllithium pentane solution (18.1 ml) was added while cooling with an ice bath under a nitrogen atmosphere. After completion of the dropwise addition, the temperature was raised to 60 ° C. and stirred for 2 hours, and then components having a lower boiling point than t-butylbenzene were distilled off under reduced pressure.
- N 1 , N 1 , N 3 -triphenylbenzene-1,3-diamine 51.7 g
- 1-bromo-2,3-dichlorobenzene 35.0 g
- Pd-132 (0. 6 g)
- NaOtBu 22.4 g
- xylene 350 ml
- N 1- (2,3-dichlorophenyl) -N 1 , N 3 , N 3 -triphenylbenzene-1,3-diamine (15.0 g), di ([1,1′-biphenyl]-
- a flask containing 4-yl) amine (10.0 g), Pd-132 (0.2 g), NaOtBu (4.5 g) and xylene (70 ml) was heated and stirred at 120 ° C. for 1 hour. After cooling the reaction solution to room temperature, water and toluene were added to separate the solution. Subsequently, it refine
- N 1, N 1 - Di ([1,1'-biphenyl] -4-yl) -2-chloro -N 3 - (3- (diphenylamino) phenyl) -N 3 - phenyl 1,3-diamine To a flask containing 18.0 g) and t-butylbenzene (130 ml) was added 1.7 M t-butyllithium pentane solution (27.6 ml) while cooling with an ice bath under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was heated to 60 ° C. and stirred for 3 hours, and components having a lower boiling point than t-butylbenzene were distilled off under reduced pressure.
- N 1- (2,3-dichlorophenyl) -N 1 , N 3 , N 3 -triphenylbenzene-1,3-diamine (14.0 g)
- N, 9-diphenyl-9H-carbazole-2 A flask containing amine (10.4 g), Pd-132 (0.2 g), NaOtBu (4.1 g) and xylene (90 ml) was heated and stirred at 120 ° C. for 1 hour. After cooling the reaction solution to room temperature, water and toluene were added to separate the solution.
- N 1- (2,3-dichlorophenyl) -N 1 , N 3 , N 3 -triphenylbenzene-1,3-diamine (15.0 g), di-p-tolylamine (6.1 g),
- the fraction containing the desired product is reprecipitated by distilling off under reduced pressure, and 2-chloro-N 1- (3- (diphenylamino) phenyl) -N 1 -phenyl-N 3 , N 3 -di-p-tolylbenzene -1,3-diamine (15.0 g) was obtained.
- N 1 , N 1 -diphenylbenzene-1,3-diamine (12.0 g), 4-bromo-1,1′-biphenyl (30.2 g), Pd-132 (0.3 g), NaOtBu
- -N 1- (3- (diphenylamino) phenyl) -N 3 , N 3 -diphenylbenzene-1,3-diamine (20.2 g) was obtained.
- N 1 -([1,1′-biphenyl] -4-yl) -2-chloro-N 1- (3- (diphenylamino) phenyl) -N 3 , N 3 -diphenylbenzene-1,3-diamine A 1.6M t-butyllithium pentane solution (26.1 ml) was added to a flask containing 16.0 g) and t-butylbenzene (100 ml) with cooling in an ice bath under a nitrogen atmosphere. After completion of the dropwise addition, the temperature was raised to 60 ° C. and stirred for 2 hours, and then components having a lower boiling point than t-butylbenzene were distilled off under reduced pressure.
- N 1- (2,3-dichlorophenyl) -N 1 , N 3 , N 3 -triphenylbenzene-1,3-diamine (15.0 g), di ([1,1′-biphenyl]-
- a flask containing 3-yl) amine (10.0 g)
- Pd-132 0.2 g
- NaOtBu 4.5 g
- xylene 70 ml
- 1.6M t-butyllithium pentane solution (32.6 ml) was added to a flask containing (20.0 g) and t-butylbenzene (150 ml) while cooling with an ice bath under a nitrogen atmosphere. After completion of the dropwise addition, the temperature was raised to 60 ° C. and stirred for 2 hours, and then components having a lower boiling point than t-butylbenzene were distilled off under reduced pressure.
- Flask containing 1,4-dibromo-2,3,5,6-tetrafluorobenzene (6.24 g), phenol (9.53 g), potassium carbonate (14.0 g) and NMP (20 ml) under nitrogen atmosphere was heated and stirred at 140 ° C. for 18 hours.
- the reaction solution was cooled to room temperature, and saturated brine and toluene were added to separate the layers.
- the residue was purified with a silica gel short pass column (developing solution: toluene).
- the solvent was distilled off under reduced pressure, and the crude product was washed with methanol to obtain 1,4-dibromo-2,3,5,6-tetraphenoxybenzene (9.64 g).
- 1.6M n-butyllithium hexane was added to a solution of 1,4-dibromo-2,3,5,6-tetraphenoxybenzene (0.604 g) in diethyl ether (4.0 ml) at 0 ° C. under a nitrogen atmosphere. Solution (1.52 ml) was added. After stirring for 1 hour, it heated up to room temperature and stirred for 1 hour. After the solvent was distilled off under reduced pressure, the mixture was cooled to 0 ° C., tetrahydrofuran (5.0 ml) and bisdiethylaminochlorophosphine (0.590 ml) were added, and the mixture was stirred for 1 hour.
- 1,4-dibromo-2,3,5,6-tetrafluorobenzene (3.08 g), 4-butylphenol (7.70 ml), potassium carbonate (6.91 g) and NMP (20 ml) are contained.
- the flask was heated and stirred at 140 ° C. for 33 hours.
- the reaction solution was cooled to room temperature, and saturated brine and toluene were added to separate the layers.
- the residue was purified with a silica gel short pass column (developing solution: toluene).
- the solvent was distilled off under reduced pressure, and the crude product was washed with methanol to obtain 1,4-dibromo-2,3,5,6-tetra (4-butylphenoxy) benzene (4.13 g). .
- N 1 , N 1 , N 3 , N 3 , N 5 , N 5 -hexakis (4-methylphenyl) -1,3,5-benzenetriamine (16.6 g, 25 mmol) and o-dichlorobenzene (150 ml) ) was added boron tribromide (4.73 ml, 50 mmol) at room temperature under a nitrogen atmosphere, and the mixture was heated and stirred at 170 ° C. for 20 hours. Thereafter, the reaction solution was distilled off under reduced pressure at 60 ° C. Filtration was performed using a Florisil short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with hexane, and the resulting solid was washed with toluene to obtain a compound (8.08 g) represented by the formula (1-2626) as a yellow solid.
- N, N-diisopropylethylamine (0.775 ml, 4.5 mmol) was added and filtered using a Florisil short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product.
- the crude product was washed with ethyl acetate to obtain a compound (0.118 g) represented by the formula (1-2665) as a yellow solid.
- N 1 , N 1 , N 3 , N 3 , N 5 , N 5 -hexakis (4-methylphenyl) -1,3,5-benzenetriamine 0.322 g, 0.5 mmol
- o-dichlorobenzene 3.0 ml
- triphenylborane 0.730 g, 3.0 mmol
- boron tribromide 0.284 ml, 3.0 mmol
- N, N-diisopropylethylamine (1.55 ml, 9.1 mmol) was added and filtered using a Florisil short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product.
- the crude product was washed with hexane, and the resulting solid was washed with ethyl acetate to obtain a compound (0.188 g) represented by the formula (1-2678) as a yellow solid. It was.
- Hexane was distilled off by heating and stirring at 100 ° C. for 1 hour under a nitrogen stream, followed by heating and stirring at 120 ° C. for 5 hours. After stirring at 150 ° C. for 16.5 hours, the solvent was distilled off under reduced pressure. Toluene was added, followed by filtration using a silica gel short pass column, and the solvent was distilled off under reduced pressure to obtain a crude product. By washing with acetonitrile, a compound represented by the formula (1-4401) was obtained as a white solid (0.101 g, yield 56%).
- polycyclic aromatic compounds of the present invention can be synthesized by a method according to the synthesis example described above by appropriately changing the raw material compound.
- the organic EL elements according to Examples 1 and 2 were manufactured, and the external quantum efficiency when driven at a current density at which a luminance of 100 cd / m 2 was obtained was measured.
- the material configuration of each layer in the produced organic EL element is shown in Table 1 below.
- HI refers to N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl] -4, 4′-diamine
- HAT-CN is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile
- HT is N-([1,1′-biphenyl] -4-yl) —N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl)-[1,1′-biphenyl] -4-amine
- BH1 is 9-phenyl-10- (4-phenylnaphthalene) -1-yl) anthracene
- ET-2 is 9- (4 ′-(dimesitylboryl)-[1,1′-binaphthalen] -4-yl) -9H-carbazole
- ET 9- (4 ′
- Example 1 ⁇ Device using Compound (1-176) as dopant material for light-emitting layer>
- a 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate manufactured by Optoscience Co., Ltd. obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate.
- This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (made by Showa Vacuum Co., Ltd.), a molybdenum vapor deposition boat containing HI, a molybdenum vapor deposition boat containing HAT-CN, and a molybdenum containing HT.
- molybdenum vapor deposition boat, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were mounted.
- the following layers were sequentially formed on the ITO film of the transparent support substrate.
- the vacuum chamber is depressurized to 5 ⁇ 10 ⁇ 4 Pa, first, the evaporation boat containing HI is heated and evaporated to a film thickness of 65 nm to form the hole injection layer 1, and then HAT-CN The evaporation boat containing was heated and evaporated to a thickness of 5 nm to form the hole injection layer 2. Furthermore, the vapor deposition boat containing HT was heated and vapor-deposited to a film thickness of 60 nm to form a hole transport layer.
- the vapor deposition boat containing BH1 and the vapor deposition boat containing the compound (1-176) were heated at the same time to form a light emitting layer by vapor deposition to a film thickness of 25 nm.
- the deposition rate was adjusted so that the weight ratio of BH1 to compound (1-176) was approximately 80:20.
- the evaporation boat containing ET-2 is heated to deposit to a film thickness of 20 nm to form the electron transport layer 2, and the evaporation boat containing ET-1 is further heated to obtain a film thickness.
- the electron transport layer 1 was formed at 10 nm.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- the deposition boat containing LiF was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- the cathode boat was formed by heating the evaporation boat containing aluminum and depositing it at a deposition rate of 0.01 to 2 nm / second so as to have a film thickness of 100 nm, thereby obtaining an organic EL device.
- Example 2 ⁇ Device using Compound (1-100) as a dopant material for the light-emitting layer>
- An organic EL device was obtained in the same manner as in Example 1 except that the compound (1-176) as the dopant material for the light emitting layer was changed to the compound (1-100).
- blue light emission having a peak top at about 457 nm was obtained.
- the external quantum efficiency at a luminance of 100 cd / m 2 was 2.78%.
- the organic EL elements according to Examples 3 and 4 were produced, and the external quantum efficiency was measured when driven at a current density at which a luminance of 100 cd / m 2 was obtained.
- the material configuration of each layer in the produced organic EL element is shown in Table 2 below.
- TPB means N 4 , N 4 , N 4 ′, N 4 ′ -tetra ([1,1′-biphenyl] -4-yl)-[1,1′-biphenyl] -4,4 '-Diamine,' CBP 'is 4,4'-di (9H-carbazolyl-9-yl) -1,1'-biphenyl,' TPBi 'is 1,3,5-tris (1-phenyl-1H-benzo [D] imidazol-2-yl) benzene.
- the chemical structure is shown below.
- Example 3 ⁇ Device Using Compound (1-141) as Dopant Material for Light-Emitting Layer>
- a 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate.
- This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing HAT-CN, a molybdenum vapor deposition boat containing TBB, and CBP were introduced.
- the following layers were sequentially formed on the ITO film of the transparent support substrate.
- Depressurize the vacuum chamber to 5 ⁇ 10 ⁇ 4 Pa first heat the evaporation boat containing HAT-CN to form a hole injection layer by vapor deposition to a film thickness of 10 nm, and then TBB The vapor deposition boat was heated and vapor deposited to a film thickness of 30 nm to form a hole transport layer.
- the vapor deposition boat containing CBP and the vapor deposition boat containing the compound (1-141) were heated at the same time to form a light emitting layer by vapor deposition to a film thickness of 30 nm.
- the deposition rate was adjusted so that the weight ratio of CBP to compound (1-141) was about 80:20.
- the evaporation boat containing TPBi was heated and evaporated to a thickness of 50 nm to form an electron transport layer.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- the deposition boat containing LiF was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- the cathode boat was formed by heating the evaporation boat containing aluminum and depositing it at a deposition rate of 0.01 to 2 nm / second so as to have a film thickness of 100 nm, thereby obtaining an organic EL device.
- Example 4 ⁇ Device using Compound (1-81) as a dopant material for the light-emitting layer>
- An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-141) as the dopant material for the light emitting layer was changed to the compound (1-81).
- a DC voltage was applied to both electrodes, green light emission having a peak top at about 512 nm was obtained.
- the external quantum efficiency at a luminance of 100 cd / m 2 was 8.37%.
- the organic EL device according to Example 5 was manufactured, and the external quantum efficiency was measured when the device was driven at a current density at which a luminance of 1000 cd / m 2 or 100 cd / m 2 was obtained.
- the material constitution of each layer in the produced organic EL element is shown in Table 3 below.
- Example 5 ⁇ Element Using Compound (1-91) as Host Material for Light-Emitting Layer> A 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate.
- This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), a molybdenum vapor deposition boat containing HAT-CN, a molybdenum vapor deposition boat containing TBB, and a compound of the present invention
- a molybdenum vapor deposition boat containing Ir (PPy) 3 a molybdenum vapor deposition boat containing TPBi
- a molybdenum vapor deposition boat containing LiF and aluminum.
- a tungsten evaporation boat was installed.
- the following layers were sequentially formed on the ITO film of the transparent support substrate. Depressurize the vacuum chamber to 5 ⁇ 10 ⁇ 4 Pa, first heat the evaporation boat containing HAT-CN to form a hole injection layer by vapor deposition to a film thickness of 10 nm, and then TBB The vapor deposition boat was heated and vapor deposited to a film thickness of 30 nm to form a hole transport layer. Next, the vapor deposition boat containing the compound (1-91) and the vapor deposition boat containing Ir (PPy) 3 were heated at the same time to form a light emitting layer by vapor deposition to a thickness of 30 nm.
- the deposition rate was adjusted so that the weight ratio of compound (1-91) to Ir (PPy) 3 was about 95: 5.
- the evaporation boat containing TPBi was heated and evaporated to a thickness of 50 nm to form an electron transport layer.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- the deposition boat containing LiF was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- the cathode boat was formed by heating the evaporation boat containing aluminum and depositing it at a deposition rate of 0.01 to 2 nm / second so as to have a film thickness of 100 nm, thereby obtaining an organic EL device.
- the organic EL elements according to Examples 6 to 14 were manufactured, and the external quantum efficiency was measured when driven at a current density at which a luminance of 1000 cd / m 2 or 100 cd / m 2 was obtained.
- the material configuration of each layer in the produced organic EL element is shown in Table 4 below.
- Example 6> ⁇ Device Using Compound (1-152) as Host Material for Light-Emitting Layer> An organic EL device was obtained in the same manner as in Example 5 except that the compound (1-91) as the host material for the light emitting layer was changed to the compound (1-152). When a DC voltage was applied to both electrodes, green light emission having a peak top at about 512 nm was obtained. The external quantum efficiency at a luminance of 1000 cd / m 2 was 9.36%. The external quantum efficiency at a luminance of 100 cd / m 2 was 13.26%.
- Example 7 ⁇ Device Using Compound (1-1048) as Host Material for Light-Emitting Layer> An organic EL device was obtained in the same manner as in Example 5 except that the compound (1-91) serving as the host material for the light-emitting layer was changed to the compound (1-1048). When a DC voltage was applied to both electrodes, green light emission having a peak top at about 512 nm was obtained. The external quantum efficiency at a luminance of 1000 cd / m 2 was 9.50%. The external quantum efficiency at a luminance of 100 cd / m 2 was 12.43%.
- Example 8 ⁇ Element Using Compound (1-1049) as Host Material for Light-Emitting Layer> An organic EL device was obtained in the same manner as in Example 5 except that the compound (1-91) as the host material for the light emitting layer was changed to the compound (1-1049). When a DC voltage was applied to both electrodes, green light emission having a peak top at about 512 nm was obtained. The external quantum efficiency at a luminance of 1000 cd / m 2 was 6.54%. The external quantum efficiency at a luminance of 100 cd / m 2 was 7.44%.
- Example 9 ⁇ Device Using Compound (1-1050) as Host Material for Light-Emitting Layer> An organic EL device was obtained in the same manner as in Example 5 except that the compound (1-91) as the host material for the light emitting layer was replaced with the compound (1-1050). When a DC voltage was applied to both electrodes, green light emission having a peak top at about 512 nm was obtained. The external quantum efficiency at a luminance of 1000 cd / m 2 was 10.98%. The external quantum efficiency at a luminance of 100 cd / m 2 was 12.32%.
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Abstract
Description
下記一般式(1)で表される多環芳香族化合物、または下記一般式(1)で表される構造を複数有する多環芳香族化合物の多量体。
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリールまたはアルキルであり、
X1およびX2は、それぞれ独立して、O、N-R、SまたはSeであり、前記N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは連結基または単結合により前記A環、B環および/またはC環と結合していてもよく、そして、
式(1)で表される化合物または構造における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい。)
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換または無置換のアリール、置換または無置換のヘテロアリール、置換または無置換のジアリールアミノ、置換または無置換のジヘテロアリールアミノ、置換または無置換のアリールヘテロアリールアミノ、置換または無置換のアルキル、置換または無置換のアルコキシまたは置換または無置換のアリールオキシで置換されていてもよく、また、これらの環はY1、X1およびX2から構成される上記式中央の縮合2環構造と結合を共有する5員環または6員環を有し、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリールまたはアルキルであり、
X1およびX2は、それぞれ独立して、O、N-R、SまたはSeであり、前記N-RのRはアルキルで置換されていてもよいアリール、アルキルで置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは-O-、-S-、-C(-R)2-または単結合により前記A環、B環および/またはC環と結合していてもよく、前記-C(-R)2-のRは水素またはアルキルであり、
式(1)で表される化合物または構造における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよく、そして、
多量体の場合には、一般式(1)で表される構造を2または3個有する2または3量体である、
上記[1]に記載する多環芳香族化合物またはその多量体。
下記一般式(2)で表される、上記[1]に記載する多環芳香族化合物。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、また、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRは炭素数6~12のアリールまたは炭素数1~6のアルキルであり、
X1およびX2は、それぞれ独立して、O、N-R、SまたはSeであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルであり、また、前記N-RのRは-O-、-S-、-C(-R)2-または単結合により前記a環、b環および/またはc環と結合していてもよく、前記-C(-R)2-のRは炭素数1~6のアルキルであり、そして、
式(2)で表される化合物における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい。)
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11は、それぞれ独立して、水素、炭素数6~30のアリール、炭素数2~30のヘテロアリールまたはジアリールアミノ(ただしアリールは炭素数6~12のアリール)であり、また、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共に炭素数9~16のアリール環または炭素数6~15のヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素は炭素数6~10のアリールで置換されていてもよく、
Y1は、B、P、P=O、P=SまたはSi-Rであり、前記Si-RのRは炭素数6~10のアリールまたは炭素数1~4のアルキルであり、
X1およびX2は、それぞれ独立して、O、N-RまたはSであり、前記N-RのRは炭素数6~10のアリールまたは炭素数1~4のアルキルであり、そして、
式(2)で表される化合物における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい、
上記[3]に記載する多環芳香族化合物。
前記ハロゲンはフッ素である、上記[1]~[4]のいずれかに記載する多環芳香族化合物またはその多量体。
下記式(1-1)、下記式(1-2)、下記式(1-4)、下記式(1-10)、下記式(1-49)、下記式(1-81)、下記式(1-91)、下記式(1-100)、下記式(1-141)、下記式(1-151)、下記式(1-176)、下記式(1-411)、下記式(1-447)、下記式(1-501)、下記式(1-601)または下記式(1-701)で表される、上記[1]に記載する多環芳香族化合物。
下記式(1-21)、下記式(1-23)、下記式(1-24)、下記式(1-50)、下記式(1-152)、下記式(1-201)、下記式(1-401)、下記式(1-422)、下記式(1-1048)、下記式(1-1049)、下記式(1-1050)、下記式(1-1069)、下記式(1-1084)、下記式(1-1090)、下記式(1-1092)、下記式(1-1101)、下記式(1-1102)、下記式(1-1103)、下記式(1-1145)、下記式(1-1152)、下記式(1-1159)、下記式(1-1187)、下記式(1-1190)、下記式(1-1191)、下記式(1-1192)、下記式(1-1201)、下記式(1-1210)、下記式(1-1247)、下記式(1-1250)、下記式(1-1251)、下記式(1-1252)または下記式(1-1271)で表される、上記[1]に記載する多環芳香族化合物。
下記式(1-1-1)、下記式(1-79)、下記式(1-142)、下記式(1-152-2)、下記式(1-158)、下記式(1-159)、下記式(1-721)、下記式(1-1006)、下記式(1-1104)、下記式(1-1149)、下記式(1-1150)、下記式(1-1301)、下記式(1-1351)、下記式(1-2305)、下記式(1-2626)、下記式(1-2657)、下記式(1-2662)、下記式(1-2665)、下記式(1-2676)、下記式(1-2678)、下記式(1-2679)、下記式(1-2680)、下記式(1-2681)、下記式(1-2682)、下記式(1-2683)、下記式(1-2691)、下記式(1-2699)、下記式(1-3588)、下記式(1-3654)、下記式(1-3690)、下記式(1-3806)、下記式(1-3824)、下記式(1-4114)、下記式(1-4150)、下記式(1-4341)、下記式(1-4346)、下記式(1-4401)、下記式(1-4421-1)で表される、上記[1]に記載する多環芳香族化合物。
上記[1]ないし[8]のいずれかに記載する多環芳香族化合物またはその多量体を含有する、有機デバイス用材料。
前記有機デバイス用材料が、有機電界発光素子用材料、有機電界効果トランジスタ用材料または有機薄膜太陽電池用材料である、上記[9]に記載する有機デバイス用材料。
発光層用材料である、上記[10]に記載する有機電界発光素子用材料。
電子注入層用材料または電子輸送層用材料である、上記[10]に記載する有機電界発光素子用材料。
正孔注入層用材料または正孔輸送層用材料である、上記[10]に記載する有機電界発光素子用材料。
陽極および陰極からなる一対の電極と、該一対の電極間に配置され、上記[11]に記載する発光層用材料を含有する発光層とを有する、有機電界発光素子。
陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層と、前記陰極および前記発光層の間に配置され、上記[12]に記載する電子注入層用材料および/または電子輸送層用材料を含有する電子注入層および/または電子輸送層とを有する、有機電界発光素子。
陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層と、前記陽極および前記発光層の間に配置され、上記[13]に記載する正孔注入層用材料および/または正孔輸送層用材料を含有する正孔注入層および/または正孔輸送層とを有する、有機電界発光素子。
さらに、前記陰極と該発光層との間に配置される電子輸送層および/または電子注入層を有し、該電子輸送層および電子注入層の少なくとも1つは、キノリノール系金属錯体、ピリジン誘導体、フェナントロリン誘導体、ボラン誘導体およびベンゾイミダゾール誘導体からなる群から選択される少なくとも1つを含有する、上記[14]~[16]のいずれかに記載する有機電界発光素子。
前記電子輸送層および/または電子注入層が、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、上記[17]に記載の有機電界発光素子。
上記[14]~[18]のいずれかに記載する有機電界発光素子を備えた表示装置。
上記[14]~[18]のいずれかに記載する有機電界発光素子を備えた照明装置。
Y1のハロゲン化物、Y1のアミノ化ハロゲン化物、Y1のアルコキシ化物およびY1のアリールオキシ化物からなる群から選択される試薬と、場合によりブレンステッド塩基とを用いて、連続的な芳香族求電子置換反応により、下記中間体におけるA環とB環とC環とを前記Y1により結合する反応工程を含む、上記[1]に記載する下記一般式(1)で表される多環芳香族化合物、または下記一般式(1)で表される構造を複数有する多環芳香族化合物の多量体を製造する方法。
有機アルカリ化合物を用いて下記中間体におけるX1とX2の間の水素原子をオルトメタル化する反応工程と、
Y1のハロゲン化物、Y1のアミノ化ハロゲン化物、Y1のアルコキシ化物およびY1のアリールオキシ化物からなる群から選択される試薬を用いて前記メタルとY1とを交換する反応工程と、
ブレンステッド塩基を用いて連続的な芳香族求電子置換反応により前記Y1でB環とC環とを結合する反応工程と
を含む、上記[1]に記載する下記一般式(1)で表される多環芳香族化合物、または下記一般式(1)で表される構造を複数有する多環芳香族化合物の多量体を製造する方法。
さらにルイス酸を加えて反応を促進させることを特徴とする、上記[21]または[22]に記載する製造方法。
さらに中間体におけるX1とX2の間の水素原子をあらかじめハロゲン化する反応工程を含む、上記[21]~[23]のいずれかに記載する製造方法。
本願発明は、下記一般式(1)で表される多環芳香族化合物、または下記一般式(1)で表される構造を複数有する多環芳香族化合物の多量体である。本願発明は、好ましくは、下記一般式(2)で表される多環芳香族化合物、または下記一般式(2)で表される構造を複数有する多環芳香族化合物の多量体である。
この規定は、下記式(2-3-1)で表される、X1やX2が縮合環B’および縮合環C’に取り込まれた環構造を有する化合物で表現できる。すなわち、例えば一般式(2)におけるb環(またはc環)であるベンゼン環に対してX1(またはX2)を取り込むようにして他の環が縮合して形成されるB’環(またはC’環)を有する化合物である。この化合物は、例えば後述する具体的化合物として列挙した、式(1-451)~(1-462)で表されるような化合物および式(1-1401)~(1-1460)で表されるような化合物に対応し、形成されてできた縮合環B’(または縮合環C’)は例えばフェノキサジン環、フェノチアジン環またはアクリジン環である。
また、上記規定は、下記式(2-3-2)や式(2-3-3)で表される、X1および/またはX2が縮合環A’に取り込まれた環構造を有する化合物でも表現できる。すなわち、例えば一般式(2)におけるa環であるベンゼン環に対してX1(および/またはX2)を取り込むようにして他の環が縮合して形成されるA’環を有する化合物である。この化合物は、例えば後述する具体的化合物として列挙した式(1-471)~(1-479)で表されるような化合物に対応し、形成されてできた縮合環A’は例えばフェノキサジン環、フェノチアジン環またはアクリジン環である。
なお、式中のRはアルキルであり、直鎖および分枝鎖のいずれでもよく、例えば、炭素数1~24の直鎖アルキルまたは炭素数3~24の分枝鎖アルキルがあげられる。炭素数1~18のアルキル(炭素数3~18の分枝鎖アルキル)が好ましく、炭素数1~12のアルキル(炭素数3~12の分枝鎖アルキル)がより好ましく、炭素数1~6のアルキル(炭素数3~6の分枝鎖アルキル)がさらに好ましく、炭素数1~4のアルキル(炭素数3~4の分枝鎖アルキル)が特に好ましい。また、Rとしては他にフェニルが挙げられる。
また、「PhO-」はフェニルオキシ基であり、このフェニルは例えば式(1-4421-1)のように直鎖または分枝鎖のアルキルで置換されていてもよく、例えば、炭素数1~24の直鎖アルキルまたは炭素数3~24の分枝鎖アルキル、炭素数1~18のアルキル(炭素数3~18の分枝鎖アルキル)、炭素数1~12のアルキル(炭素数3~12の分枝鎖アルキル)、炭素数1~6のアルキル(炭素数3~6の分枝鎖アルキル)、炭素数1~4のアルキル(炭素数3~4の分枝鎖アルキル)で置換されていてもよい。
具体的には、以下の式(1-1-R)~式(1-4401-R)で表される化合物が挙げられる。下記式中のRはそれぞれ独立して炭素数1~12のアルキルまたは炭素数6~10のアリール、好ましくは炭素数1~4のアルキルまたはフェニルであり、nはそれぞれ独立して0~2、好ましくは1である。
一般式(1)や(2)で表される多環芳香族化合物およびその多量体は、基本的には、まずA環(a環)とB環(b環)およびC環(c環)とを結合基(X1やX2を含む基)で結合させることで中間体を製造し(第1反応)、その後に、A環(a環)、B環(b環)およびC環(c環)を結合基(Y1を含む基)で結合させることで最終生成物を製造することができる(第2反応)。第1反応では、例えばエーテル化反応であれば、求核置換反応、ウルマン反応といった一般的反応が利用でき、アミノ化反応で有ればブッフバルト-ハートウィッグ反応といった一般的反応が利用できる。また、第2反応では、タンデムヘテロフリーデルクラフツ反応(連続的な芳香族求電子置換反応、以下同様)が利用できる。
本発明に係る多環芳香族化合物およびその多量体は、例えば、有機電界発光素子の材料として用いることができる。以下に、本実施形態に係る有機EL素子について図面に基づいて詳細に説明する。図1は、本実施形態に係る有機EL素子を示す概略断面図である。
図1に示された有機電界発光素子100は、基板101と、基板101上に設けられた陽極102と、陽極102の上に設けられた正孔注入層103と、正孔注入層103の上に設けられた正孔輸送層104と、正孔輸送層104の上に設けられた発光層105と、発光層105の上に設けられた電子輸送層106と、電子輸送層106の上に設けられた電子注入層107と、電子注入層107の上に設けられた陰極108とを有する。
基板101は、有機電界発光素子100の支持体となるものであり、通常、石英、ガラス、金属、プラスチックなどが用いられる。基板101は、目的に応じて板状、フィルム状、またはシート状に形成され、例えば、ガラス板、金属板、金属箔、プラスチックフィルム、プラスチックシートなどが用いられる。なかでも、ガラス板、および、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホンなどの透明な合成樹脂製の板が好ましい。ガラス基板であれば、ソーダライムガラスや無アルカリガラスなどが用いられ、また、厚みも機械的強度を保つのに十分な厚みがあればよいので、例えば、0.2mm以上あればよい。厚さの上限値としては、例えば、2mm以下、好ましくは1mm以下である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、SiO2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することができる。また、基板101には、ガスバリア性を高めるために、少なくとも片面に緻密なシリコン酸化膜などのガスバリア膜を設けてもよく、特にガスバリア性が低い合成樹脂製の板、フィルムまたはシートを基板101として用いる場合にはガスバリア膜を設けるのが好ましい。
陽極102は、発光層105へ正孔を注入する役割を果たすものである。なお、陽極102と発光層105との間に正孔注入層103および/または正孔輸送層104が設けられている場合には、これらを介して発光層105へ正孔を注入することになる。
正孔注入層103は、陽極102から移動してくる正孔を、効率よく発光層105内または正孔輸送層104内に注入する役割を果たすものである。正孔輸送層104は、陽極102から注入された正孔または陽極102から正孔注入層103を介して注入された正孔を、効率よく発光層105に輸送する役割を果たすものである。正孔注入層103および正孔輸送層104は、それぞれ、正孔注入・輸送材料の一種または二種以上を積層、混合するか、正孔注入・輸送材料と高分子結着剤の混合物により形成される。また、正孔注入・輸送材料に塩化鉄(III)のような無機塩を添加して層を形成してもよい。
発光層105は、電界を与えられた電極間において、陽極102から注入された正孔と、陰極108から注入された電子とを再結合させることにより発光するものである。発光層105を形成する材料としては、正孔と電子との再結合によって励起されて発光する化合物(発光性化合物)であればよく、安定な薄膜形状を形成することができ、かつ、固体状態で強い発光(蛍光)効率を示す化合物であるのが好ましい。本発明では、発光層用の材料として、上記一般式(1)で表される多環芳香族化合物またはその多量体を用いることができる。
また、特開2003-347056号公報、および特開2001-307884号公報などに記載されたスチルベン構造を有するアミンを用いてもよい。
また、特開平11-97178号公報、特開2000-133457号公報、特開2000-26324号公報、特開2001-267079号公報、特開2001-267078号公報、特開2001-267076号公報、特開2000-34234号公報、特開2001-267075号公報、および特開2001-217077号公報などに記載されたペリレン誘導体を用いてもよい。
また、国際公開第2000/40586号パンフレットなどに記載されたボラン誘導体を用いてもよい。
また、特開2006-156888号公報などに記載された芳香族アミン誘導体を用いてもよい。
また、特開2004-43646号公報、特開2001-76876号公報、および特開平6-298758号公報などに記載されたクマリン誘導体を用いてもよい。
電子注入層107は、陰極108から移動してくる電子を、効率よく発光層105内または電子輸送層106内に注入する役割を果たすものである。電子輸送層106は、陰極108から注入された電子または陰極108から電子注入層107を介して注入された電子を、効率よく発光層105に輸送する役割を果たすものである。電子輸送層106および電子注入層107は、それぞれ、電子輸送・注入材料の一種または二種以上を積層、混合するか、電子輸送・注入材料と高分子結着剤の混合物により形成される。
陰極108は、電子注入層107および電子輸送層106を介して、発光層105に電子を注入する役割を果たすものである。
以上の正孔注入層、正孔輸送層、発光層、電子輸送層および電子注入層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ(N-ビニルカルバゾール)、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルホン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリアミド、エチルセルロース、酢酸ビニル樹脂、ABS樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
有機電界発光素子を構成する各層は、各層を構成すべき材料を蒸着法、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、印刷法、スピンコート法またはキャスト法、コーティング法などの方法で薄膜とすることにより、形成することができる。このようにして形成された各層の膜厚については特に限定はなく、材料の性質に応じて適宜設定することができるが、通常2nm~5000nmの範囲である。膜厚は通常、水晶発振式膜厚測定装置などで測定できる。蒸着法を用いて薄膜化する場合、その蒸着条件は、材料の種類、膜の目的とする結晶構造および会合構造などにより異なる。蒸着条件は一般的に、ボート加熱温度+50~+400℃、真空度10-6~10-3Pa、蒸着速度0.01~50nm/秒、基板温度-150~+300℃、膜厚2nm~5μmの範囲で適宜設定することが好ましい。
また、本発明は、有機電界発光素子を備えた表示装置または有機電界発光素子を備えた照明装置などにも応用することができる。
有機電界発光素子を備えた表示装置または照明装置は、本実施形態にかかる有機電界発光素子と公知の駆動装置とを接続するなど公知の方法によって製造することができ、直流駆動、パルス駆動、交流駆動など公知の駆動方法を適宜用いて駆動することができる。
本発明に係る多環芳香族化合物およびその多量体は、上述した有機電界発光素子の他に、有機電界効果トランジスタまたは有機薄膜太陽電池などの作製に用いることができる。
(1)基板/ゲート電極/絶縁体層/ソース電極・ドレイン電極/有機半導体活性層
(2)基板/ゲート電極/絶縁体層/有機半導体活性層/ソース電極・ドレイン電極
(3)基板/有機半導体活性層/ソース電極・ドレイン電極/絶縁体層/ゲート電極
(4)基板/ソース電極・ドレイン電極/有機半導体活性層/絶縁体層/ゲート電極
このように構成された有機電界効果トランジスタは、アクティブマトリックス駆動方式の液晶ディスプレイや有機エレクトロルミネッセンスディスプレイの画素駆動スイッチング素子等として適用できる。
1H-NMR(400MHz,CDCl3):δ=8.69(dd,2H)、7.79(t,1H)、7.70(ddd,2H)、7.54(dt,2H)、7.38(ddd,2H)、7.22(d,2H).
1H-NMR(400MHz,CDCl3):δ=8.82-8.85(m,2H)、8.71(d,2H)、7.94-7.97(m,2H)、7.89(t,1H)、7.78(d,2H)、7.66-7.71(m,4H)、7.48(d,2H)
1H-NMR(400MHz,CDCl3):δ=8.96(m,2H)、7.97(dd,2H)、7.83(t,1H)、7.74(m,4H)、7.64(d,2H)、7.51(t,4H)、7.40(t,2H)、7.28(d,2H).
1H-NMR(400MHz,CDCl3):δ=8.74(d,2H)、8.00(s,1H)、7.81(d,4H)、7.69(t,2H)、7.54(t,4H)、7.49(m,2H)、7.37-7.46(m,4H).
1H-NMR(400MHz,CDCl3):δ=8.77(d,2H)、8.25(s,1H)、8.21(d,4H)、7.61(t,2H)、7.42(m,6H)、7.33(m,8H)、7.10(d,2H).
N6,N6,N8,N8-テトラフェニル-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセン-6,8-ジアミンの合成
1H-NMR(400MHz,CDCl3):δ=8.60(d,2H)、7.80(s,1H)、7.55(t,2H)、7.30(t,2H)、7.22(m,8H)、7.12(m,8H)、7.02(d,2H)、6.94(t,4H).
1H-NMR(400MHz,CDCl3):δ=9.61(s,2H)、8.42(m,2H)、7.64-7.77(m,9H)、7.52-7.58(m,2H)、7.42-7.51(m,8H)、7.13(d,2H).
1H-NMR(400MHz,CDCl3):δ=8.35(d,2H)、7.61(t,1H)、7.34(t,8H)、7.23(d,8H)、7.15(t,4H)、7.02(m,4H)、6.98(m,2H).
1H-NMR(400MHz,CDCl3):δ=8.75(d,2H)、8.18(d,2H)、7.75(t,2H)、7.71(d,2H)、7.58(d,2H)、7.50(s,2H)、7.42-7.49(m,4H)、7.35(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.73(d,2H)、7.75(t,2H)、7.56(d,2H)、7.44(t,2H)、7.25(s,2H)、6.57-6.80(m,6H)、6.13(br,2H).
1H-NMR(400MHz,CDCl3):δ=8.73(dd,2H)、7.75(t,1H)、7.67(m,2H)、7.57(dd,2H)、7.29(m,2H)、7.00(d,2H)、3.91(s,6H).
1H-NMR(400MHz,CDCl3):δ=8.14(m,2H)、7.55(m,2H)、7.53(t,1H)、7.35-7.37(m,4H)、7.12(dd,2H).
13C NMR (δppm in CDCl3); 102.5(d, 1C, J = 82.8 Hz), 112.8 (d, 2C, J = 4.8 Hz), 119.7 (d, 2C, J = 92.4 Hz), 119.8 (d, 2C, J = 5.8 Hz), 125.1 (d, 2C, J = 10.6 Hz), 129.0 (d, 2C, J = 6.7 Hz), 132.9 (2C), 133.2, 155.7 (2C), 156.1 (2C)
1H-NMR(400MHz,CDCl3):δ=8.22(m,2H)、7.64(dd,2H)、7.62(t,1H)、7.39-7.43(m,4H)、7.17(dd,2H).
1H NMR (δppm in CDCl3); 7.16 (dd, 2H, J = 4.0 Hz, 8.4 Hz), 7.37-7.44 (m, 4H), 7.61 (t, 1H, J = 8.4 Hz), 7.62 (dd, 2H, J = 1.6 Hz, 7.6 Hz), 8.21 (ddd, 2H, J = 1.6 Hz, 7.6 Hz, 12.0 Hz)
13C NMR (δppm in CDCl3); 103.7(d, 1C, J = 98.2 Hz), 112.2 (d, 2C , J = 4.8 Hz), 117.6 (d, 2C , J = 116.3 Hz), 119.9 (d, 2C , J = 5.8 Hz), 124.5 (d, 2C , J = 11.5 Hz), 129.4 (d, 2C , J = 4.8 Hz), 133.6 (2C), 134.1, 156.6 (2C), 157.4 (2C)
1H-NMR(400MHz,CDCl3):δ=7.77(m,2H)、7.33(m,2H)、7.25(m,1H)、7.18-7.22(m,4H)、6.93(dd,2H).
1H NMR (δppm in CDCl3); 6.94 (dd, 2H, J = 2.0 Hz, 8.4 Hz), 7.18-7.22 (m, 4H), 7.25 (dt, 1H, J = 1.2 Hz, 8.4 Hz), 7.33 (ddd, 2H, J = 0.8 Hz, 1.6 Hz, 7.6 Hz), 7.77 (ddd, 2H, J = 1.6 Hz, 6.4 Hz, 7.6 Hz)
13C NMR (δppm in CDCl3); 107.2 (d, 1C, J = 4.8 Hz), 112.5 (2C), 118.7 (2C), 121.5 (d, 2C, J = 28.0 Hz), 124.6 (d, 2C, J = 3.8 Hz), 129.7 (d, 2C, J = 4.8 Hz), 129.8, 129.9 (2C), 153.7 (d, 2C, J = 8.7 Hz), 154.5 (d, 2C, J = 6.8 Hz)
1H-NMR(400MHz,CDCl3):δ=8.16(d,2H)、7.91(d,2H)、7.80(t,1H)、7.76(d,2H)、7.74(d,2H)、7.42(dd,2H)、7.39(d,2H)、7.09(dd,2H).
1H-NMR(400MHz,CDCl3):δ=8.89(dd,2H)、7.47(t,4H)、7.39(m,4H)、7.24(m,6H)、7.10(m,4H)、6.94(m,6H)、6.72(d,2H)、5.22(m,2H).
1H NMR (400MHz,CDCl3) δ 5.62 (brs, 2H), 6.71 (d, 2H), 6.90-6.93 (m, 6H), 7.05-7.09 (m, 4H), 7.20-7.27(m, 6H), 7.33-7.38 (m, 4H), 7.44-7.48 (m, 4H), 8.90 (dd, 2H)
13C NMR (101MHz,CDCl3) δ 98.4 (2C), 116.8 (2C), 119.7 (2C), 123.5 (2C), 125.6 (4C), 128.1 (2C), 128.8 (4C), 130.2 (4C), 130.4 (2C), 130.7 (4C), 134.8 (2C), 142.1 (2C), 146.6 (2C), 147.7 (2C), 147.8 (2C), 151.1
1H-NMR(400MHz,CDCl3):δ=8.75(d,2H)、7.75-7.84(m,7H)、7.65(d,2H)、7.53(t,4H)、7.44(t,2H)、7.25(d,2H).
1H-NMR(400MHz,CDCl3):δ=9.00(m,2H)、8.03(s,1H)、7.96(dd,2H)、7.84(d,4H)、7.75(d,4H)、7.50-7.60(m,10H)、7.46(t,2H)、7.40(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.76(d,2H)、7.98(s,1H)、7.82(d,4H)、7.71(d,4H)、7.64(m,4H)、7.55(t,4H)、7.50(t,4H)、7.40-7.47(m,4H).
1H-NMR(400MHz,CDCl3):δ=8.78(d,2H)、7.81(s,1H)、7.68(d,2H)、7.48(t,2H)、7.38(d,4H)、7.35(d,4H)、7.27(m,2H)、7.19(m,6H)、7.10(t,4H).
1H-NMR(400MHz,CDCl3):δ=8.34(d,2H)、7.79(s,1H)、7.71(d,4H)、7.43(t,4H)、7.34(t,2H)、7.05-7.15(m,16H)、6.90(m,4H)、2.34(s,12H).
1H-NMR(400MHz,CDCl3):δ=8.73(d,2H)、8.17(d,2H)、8.01(d,2H)、7.74(m,4H)、7.60(d,2H)、7.58(s,2H)、7.53(d,2H)、7.40-7.48(m,4H)、7.32(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.98(m,1H)、8.80(d,1H)、8.18(d,2H)、8.04(dd,1H)、7.96(d,2H)、7.84(t,1H)、7.72-7.78(m,3H)、7.70(d,1H)、7.60(d,1H)、7.54(d,2H)、7.43-7.48(m,3H)、7.26-7.34(m,4H).
1H-NMR(400MHz,CDCl3):δ=8.81(d,1H)、8.75(d,1H)、8.18(d,2H)、8.00(d,2H)、7.89(m,1H)、7.83(t,1H)、7.71-7.77(m,4H)、7.58(d,1H)、7.53(d,2H)、7.41-7.48(m,3H)、7.26-7.34(m,4H).
1H-NMR(400MHz,CDCl3):δ=8.77(t,2H)、8.19(d,2H)、7.96(d,2H)、7.86(d,1H)、7.80(t,1H)、7.72-7.77(m,3H)、7.59(d,3H)、7.54(t,1H)、7.47(t,2H)、7.44(t,1H)、7.33(t,2H)、7.26(m,1H)、7.19(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.75(d,2H)、8.19(d,2H)、8.02(m,3H)、7.70-7.78(m,4H)、7.54-7.62(m,4H)、7.38-7.50(m,5H)、7.32(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.76(dd,2H)、8.48(s,2H)、8.26(t,2H)、7.73-7.86(m,6H)、7.58-7.67(m,6H)、7.41-7.57(m,9H)、7.38(t,1H)、7.33(m,1H).
1H-NMR(400MHz,CDCl3):δ=8.87(m,2H)、7.98(d,2H)、7.85(d,1H)、7.75(t,1H)、7.67(d,1H)、7.62(m,3H)、7.51(m,2H)、7.30-7.43(m,4H)、7.02(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.76(d,1H)、8.71(d,1H)、8.32(d,1H)、8.23(d,1H)、8.18(m,4H)、7.95-8.05(m,4H)、7.79(t,1H)、7.64(d,1H)、7.45(m,3H)、7.35(t,1H)、6.97(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.29(m,2H)、7.56(d,2H)、7.53(s,1H)、7.47(t,2H)、7.16-7.23(m,12H)、7.07-7.10(m,8H).
1H-NMR(400MHz,CDCl3):δ=8.94(d,2H)、7.70(t,4H)、7.60(t,2H)、7.42(t,2H)、7.38(d,4H)、7.26(m,3H)、6.76(d,2H)、6.14(d,2H).
1H-NMR(400MHz,CDCl3):δ=9.17(s,1H)、8.99(d,1H)、7.95(d,2H)、7.68-7.78(m,7H)、7.60(t,1H)、7.40-7.56(m,10H)、7.36(t,1H)、7.30(m,2H)、6.95(d,1H)、6.79(d,1H)、6.27(d,1H)、6.18(d,1H).
5,9,11,15-テトラフェニル-5,9,11,15-テトラヒドロ-5,9,11,15-テトラアザ-19b,20b-ジボラナフト[3,2,1-de:1’,2’,3’-jk]ペンタセンの合成
1H-NMR(400MHz,DMSO-d6):δ=10.38(s,1H)、9.08(d,2H)、7.81(t,4H)、7.70(t,2H)、7.38-7.60(m,14H)、7.30(t,2H)、7.18(d,4H)、6.74(d,2H)、6.07(d,2H)、6.02(d,2H)、5.78(s,1H).
N1-(5,9-ジフェニル-5,9-ジヒドロ-5,9-ジアザ-13b-ボラナフト[3,2,1-de]アントラセン-3-イル)-N1,N3,N3-トリフェニルベンゼン-1,3-ジアミンの合成
1H-NMR(400MHz,DMSO-d6):δ=8.78(d,1H)、8.66(d,1H)、7.69(t,2H)、7.59(t,1H)、7.59(t,2H)、7.49(m,2H)、7.40(d,2H)、7.22-7.32(m,10H)、7.18(t,1H)、6.97-7.07(m,9H)、6.89(d,1H)、6.60-6.70(m,4H)、6.11(s,1H)、5.96(m,2H).
1H-NMR(400MHz,CDCl3):δ=8.92(d,1H)、8.78(d,1H)、7.70(t,2H)、7.66(t,1H)、7.61(t,1H)、7.53(m,2H)、7.47(t,1H)、7.37(m,3H)、7.27(t,1H)、7.11(d,1H)、6.80(d,1H)、6.31(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.81(d,1H)、8.57(d,1H)、7.70(t,2H)、7.61(t,1H)、7.44(m,2H)、7.37(t,6H)、7.12-7.30(m,7H)、7.03(m,2H)、6.92(d,1H)、6.76(d,1H)、6.26(d,1H).
1H-NMR(400MHz,CDCl3):δ=9.56(s,2H)、8.28(d,2H)、7.74(m,2H)、7.50-7.66(m,15H)、6.90(d,2H).
1H-NMR(400MHz,CDCl3):δ=8.30(d,2H)、7.72(d,2H)、7.54-7.62(m,4H)、7.50(t,1H)、7.43(t,2H).
1H NMR(δppm in CDCl3);8.80(dd,J=1.6,7.8 Hz,4H)、7.83(ddd,J=1.6,6.0,8.4 Hz,4H)、7.81(dd,J=2.0,8.4 Hz,4H)、7.46(ddd,J=2.0,6.0,7.8 Hz,4H).
LRMS(EI+) m/z 462(M+)
19b,20b-ジボラ-5,9,11,15-テトラオキサジナフト[3,2,1-de:1’,2’,3’-jk]ペンタセンの合成
1H NMR(δppm in CDCl3);10.13 (s, 1H), 8.92 (dd, J = 1.6, 8.0 Hz, 2H), 7.82 (t, J = 8.0 Hz, 2H), 7.78 (ddd, J = 1.6, 6.8, 8.0 Hz, 2H), 7.62 (d, J = 7.6 Hz, 4H), 7.51-7.54 (m, 4H), 6.98 (s, 1H).
LRMS(EI+) m/z 462 (M+)
1H NMR(δppm in DMSO-D6);8.92 (d, J = 8.8 Hz, 1H), 8.77 (dd, J = 1.6, 7.6 Hz, 1H), 8.57 (d, J = 8.4 Hz, 1H), 7.93 (t, J = 8.0 Hz, 1H), 7.81 (ddd, J = 1.6, 7.2, 8.4 Hz, 1H), 7.67 (t, J = 8.0 Hz, 1H), 7.58-7.63 (m, 2H), 7.47-7.50 (m, 3H), 7.35 (dd, J = 1.6, 8.4 Hz, 1H), 7.31 (t, J = 8.0 Hz, 1H), 7.28 (d, J = 8.4 Hz, 1H), 7.19 (t, J = 8.0 Hz, 2H).
LRMS(EI+) m/z 462 (M+)
1H NMR(δppm in CDCl3);7.33 (dd, JHP = 6.2 Hz, J = 8.7 Hz, 2H), 7.38-7.55 (m, 12H), 7.68 (d, J = 7.2 Hz, 4H), 7.63 (d, J = 7.3 Hz, 4H), 7.71 (s, 1H), 7.74 (dd, JHP = 2.2 Hz, J = 8.7 Hz, 2H), 8.41 (dd, JHP = 13.4 Hz, J = 2.2 Hz, 2H).
13C NMR(δppm in CDCl3);103.2 (d, JCP = 81.9 Hz), 119.9 (d, JCP = 81.4 Hz, 2C), 120.3(2C), 126.9(2C), 127.0(4C), 127.3 (d, JCP = 7.3 Hz, 2C), 127.8 (2C), 128.0 (2C), 128.4 (4C), 129.1 (4C), 129.6 (4C), 131.7 (2C), 135.9, 136.0 (2C), 138.6 (d, JCP = 10.1 Hz, 2C), 139.3 (2C), 151.8(2C), 155.2 (2C).
1H NMR(δppm in CDCl3);7.37-7.56 (m, 14H), 7.62 (d, J = 7.3 Hz, 4H), 7.69 (d, J = 7.9 Hz, 4H), 7.79 (s, 1H), 7.80 (dd, J = 2.3, 8.7 Hz, 2H), 8.44 (dd, J = 2.3 Hz, 2H).
13C NMR(δppm in CDCl3);104.0 (d, JCP = 97.3 Hz), 117.6 (d, JCP = 116.6 Hz, 2C), 120.4 (2C), 126.3 (2C), 127.0 (4C), 127.4 (d, JCP = 4.8 Hz, 2C), 127.7 (2C), 127.9 (2C), 128.4 (4C), 129.0 (4C), 129.6 (4C), 132.4 (2C), 136.0, 136.7 (2C), 138.0 (d, JCP= 10.6 Hz, 2C), 139.3 (2C), 152.1 (2C), 156.7 (2C).
1H NMR(δppm in CDCl3);7.17 (dd, JHP = 4.1 Hz, J = 8.2 Hz, 2H), 7.41 (tt, J = 1.4, 7.3 Hz, 2H), 7.46 (dd, JHP = 2.3 Hz, J = 8.7 Hz, 2H), 7.49 (dd, J = 7.3, 8.0 Hz, 4H), 7.57 (t, J = 8.2 Hz 1H), 7.63 (d, J = 8.0 Hz, 4H), 7.78 (dd, J = 2.3, 8.7 Hz, 2H), 8.39 (dd J = 2.3 Hz, JHP = 13.5 Hz, 2H).
13C NMR(δppm in CDCl3);102.4 (d, JCP = 82.4 Hz), 112.9 (d, JCP = 4.8 Hz, 2C), 120.1 (d, JCP = 92 Hz, 2C), 120.3 (d, JCP = 6.7 Hz 2C), 127.0 (4C), 127.5 (d, JCP = 5.8 Hz, 2C), 127.9 (2C), 129.1 (4C), 131.7 (JCP = 1.9 Hz, 2C), 133.3, 138.5 (JCP = 11.5 Hz, 2C), 139.3 (2C), 155.1 (JCP =2.9 Hz, 2C), 156.2 (2C).
1H NMR(δppm in CDCl3); 7.20 (dd, JHP = 4.1 Hz, J = 8.5 Hz, 2H), 7.41 (tt, J= 1.4, 7.4 Hz, 2H), 7.48 (d, J = 7.4 Hz, 2H), 7.52 (d, J = 8.7, Hz, 4H), 7.62 (dd, J = 1.4, 7.5 Hz, 4H), 7.64 (t, J = 8.5 Hz, 1H), 7.83 (dd, J = 2.2, 8.7 Hz, 2H ), 8.41 (dd, JHP= 12.4 Hz, J = 2.2 Hz, 2H ).
13C NMR(δppm in CDCl3); 103.6 (d, JCP = 97.8 Hz), 112.4 (d, JCP = 4.8 Hz, 2C), 118.0 (d, JCP = 116.0 Hz, 2C), 120.5 (d, JCP = 6.7 Hz, 2C), 127.1 (4C), 127.5 (d, JCP = 5.8 Hz, 2C), 128.0 (2C), 129.2 (4C), 132.6 (2C), 134.3, 138.0 (d, JCP = 10.5 Hz, 2C), 139.5 (2C), 156.8 (2C), 156.8 (d, JCP = 6.9 Hz, 2C).
1H NMR(δppm in CDCl3);7.40-7.50 (m, 10H), 7.52 (dd, J = 7.2 Hz, 7.6 Hz, 4H), 7.59 (d, J = 7.2 Hz, 4H), 7.63 (ddd, JHP = 1.8 Hz, J = 1.8 Hz, 8.0 Hz, 2H), 7.67-7.70 (m, 5H), 8.26 (dd, JHP =12.8 Hz, J = 8.0 Hz, 2H).
13C NMR(δppm in CDCl3);103.5 (d, JCP = 80.5 Hz), 117.9 (d, JCP = 93.9 Hz, 2C), 118.2 (d, JCP = 5.8 Hz, 2C), 124.2 (d, JCP = 11.5 Hz, 2C), 126.9 (d, JCP = 5.8 Hz, 2C), 127.3 (4C), 127.7 (2C), 128.4 (4C), 128.6 (2C), 129.0 (4C), 129.3 (d, JCP = 5.8 Hz, 2C), 129.6 (4C), 135.9, 136.1 (2C), 139.0 (2C), 146.3 (2C), 151.7 (2C), 156.1 (2C).
1H NMR(δppm in CDCl);7.40-7.50 (m, 10H), 7.53 (t, J = 7.1 Hz, 4H), 7.61 (d, J = 6.9 Hz, 4H), 7.64 (dt, JHP= 1.9 Hz, J = 1.9 Hz, 8.0 Hz, 2H), 7.69 (d, J = 7.1 Hz, 4H), 7.77 (s, 1H), 8.32 (dd, JHP = 11.7 Hz, J = 8.0 Hz, 2H).
13C NMR(δppm in CDCl);104.3 (d, JCP = 96.8 Hz), 115.9 (d, JCP = 117.9 Hz, 2C), 118.2 (d, JCP = 5.8 Hz, 2C), 123.5 (d, JCP = 10.5 Hz, 2C), 126.3 (d, JCP = 4.8 Hz, 2C), 127.3 (4C), 127.7 (2C), 128.5 (4C), 128.6 (2C), 129.0 (4C), 129.6 (4C), 129.7 (d, JCP = 8.6 Hz, 2C), 136.1, 136.7 (2C), 139.0 (2C), 146.9 (2C), 152.2 (2C), 157.7 (2C).
1H-NMR(400MHz,CDCl3):δ=8.70(dd,2H)、7.72(t,2H)、7.66(d,2H)、7.56(d,2H)、7.46(s,2H)、7.40(t,2H)、7.30(t,4H)、7.19(m,6H)、7.08(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.73(dd,2H)、8.08(m,2H)、7.73(t,2H)、7.57(d,2H)、7.54(d,1H)、7.37-6.46(m,7H)、7.24(m,4H)、7.11(d,4H)、6.97(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.72(m,2H)、7.91(d,1H)、7.65-7.75(m,4H)、7.57(d,1H)、7.50(d,1H)、7.39(m,2H)、7.30(m,5H)、7.22(m,6H)、7.25(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.73(d,2H)、8.01(s,1H)、7.70(m,6H)、7.52(d,2H)、7.40(t,2H)、7.19-7.35(m,20H)、7.06(t,4H).
1H-NMR(400MHz,CDCl3):δ=8.68(m,2H)、8.06(m,4H)、7.92(t,1H)、7.89(dd,2H)、7.80(d,2H)、7.38(m,6H)、7.20(m,8H).
1H-NMR(400MHz,CDCl3):δ=8.96(d,2H)、8.19(d,4H)、7.87(m,3H)、7.70(m,6H)、7.49(t,4H)、7.36(t,4H)、7.33(d,2H).
1H-NMR(400MHz,CDCl3):δ=8.75(d,2H)、7.81(t,1H)、7.54(m,2H)、7.28-7.40(m,8H)、7.25(m,4H)、2.39(s,6H).
1H-NMR(400MHz,CDCl3):δ=10.00(s,1H)、8.97(d,1H)、8.86(d,1H)、8.75(d,1H)、8.72(s,1H)、8.67(m,2H)、7.86(t,1H)、7.67-7.83(m,5H)、7.63(d,1H)、7.56(t,1H)、7.31(d,1H)、7.28(d,1H).
1H-NMR(400MHz,CDCl3):δ=9.10(br,1H)、7.80-8.20(m,20H).
1H-NMR(400MHz,CDCl3):δ=8.19(br,1H)、8.14(br,1H)、7.92-8.00(m,4H)、7.89(br,1H)、7.78(br,1H)、7.30-7.76(m,12H)、7.05(br,1H).
1H-NMR(400MHz,CDCl3):δ=8.60(d,2H)、8.25(m,2H)、8.03(br,1H)7.85-7.99(m,6H)、7.66(m,4H)、7.50-7.62(m,6H).
1H-NMR(400MHz,CDCl3):δ=8.64(d,2H)、8.28(t,2H)、7.85-8.05(m,7H)、7.68(m,4H)、7.48-7.62(m,6H).
1H-NMR(400MHz,CDCl3):δ=8.21-8.30(m,2H)、8.18(d,2H)、7.87(d,2H)、7.80(d,1H)、7.73(d,2H)、7.67(t,1H)、7.63(d,1H)、7.56(d,2H)、7.29-7.50(m,9H).
1H-NMR(400MHz,CDCl3):δ=9.00-9.10(m,1H)、8.19-8.32(m,4H)、7.26-7.95(m,10H)、6.68-6.98(m,1H)).
1H-NMR(400MHz,CDCl3):δ=8.96(m,1H)、8.64(m,1H)、8.18-8.29(m,2H)、7.98(m,1H)、7.71-7.78(m,5H)、7.66(t,1H)、7.58(t,1H)、7.37-7.49(m,4H)、7.26-7.37(m,2H).
3,7-ジフェニル-3,7-ジヒドロ-3,7-ジアザ-11b-ボラナフト[3,2,1-no]テトラフェンの合成
1H-NMR(400MHz,CDCl3):δ=8.94(m,1H)、8.50(d,1H)、7.80(m,1H)、7.77(d,1H)、7.70(m,4H)、7.61(m,2H)、7.46(m,2H)、7.35-7.44(m,5H)、7.25(m,1H)、7.03(t,1H)、6.95(d,1H)、6.77(d,1H)、6.23(d,1H)、6.18(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.97(m,2H)、8.18(d,1H)、8.03(d,1H)、7.92(m,2H)、7.70(t,2H)、7.56-66(m,3H)、7.36-48(m,5H)、7.20-7.32(m,3H)、6.78(t,2H)、6.15(m,2H).
1H-NMR(400MHz,CDCl3):δ=8.65(d,2H)、7.44(t,4H)、7.33(t,2H)、7.20(m,12H)、7.13(t,1H)、7.08(m,8H)、7.00(t,4H)、6.89(dd,2H)、6.16(m,2H)、6.03(d,2H).
1H-NMR(400MHz,CDCl3):δ=9.09(m,1H)、8.79(d,1H)、7.93(d,2H)、7.75(d,2H)、7.72(d,2H)、7.67(m,1H)、7.52(t,2H)、7.40-7.50(m,7H)、7.27-7.38(m,2H)、7.19-7.26(m,7H)、7.11(m,4H)、7.03(t,2H)、6.96(dd,1H)、6.90(d,1H)、6.21(m,2H)、6.12(d,1H).
N,N,5,9,11-ペンタフェニル-9,11-ジヒドロ-5H-5,9,11-トリアザ-16b-ボラインデノ[2,1-b]ナフト[1,2,3-fg]アントラセン-3-アミンの合成
1H-NMR(400MHz,CDCl3):δ=9.57(s,1H)、8.93(d,1H)、8.26(d,1H)、7.61(t,2H)、7.10-7.50(m,25H)、7.04(m,3H)、6.59(s,1H)、6.25(m,1H)、6.10(t,2H).
1H-NMR(400MHz,CDCl3):δ=8.86(d,1H)、8.73(d,1H)、8.43(d,1H)、8.24(d,1H)、7.31-7.56(m,13H)、7.29(dd,1H)、7.12-24(m,8H)、7.10(m,4H)、7.02(t,2H)、6.94(dd,1H)、6.79(d,1H)、6.16(m,2H)、6.07(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.74(d,1H)、8.64(m,1H)、7.42-7.50(m,4H)、7.35(t,1H)、7.15-7.25(m,10H)、7.10(d,4H)、7.02(t,2H)、7.94(dd,1H)、6.68(d,1H)、6.20(m,1H)、6.11(d,1H)、6.04(d,1H)、2.52(s,3H)、2.48(s,3H).
1H-NMR(400MHz,CDCl3):δ=8.87(d,1H)、8.74(d,1H)、7.68(t,2H)、7.64(d,2H)、7.58(m,3H)、7.50(t,2H)、7.36-7.44(m,4H)、7.16-7.28(m,8H)、7.10(m,4H)、6.97(m,3H)、6.72(d,1H)、6.22(m,2H)、6.10(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.73(d,1H)、8.20(d,1H)、7.65-7.80(m,3H)、7.56-7.64(d,2H)、7.38-7.54(m,3H)、7.20-7.37(m,3H)、7.16(m,1H)、7.11(m,1H)、7.05(t,1H)、6.97(t,1H)、6.77(d,1H)、6.27(d,1H)).
1H-NMR(400MHz,CDCl3):δ=8.93(d,1H)、8.77(d,1H)、7.84(m,1H)、7.77(t,1H)、7.68(m,3H)、7.33-7.50(m,12H)、7.30(t,1H)、7.22(m,7H)、7.11(m,4H)、7.03(m,3H)、6.97(dd,1H)、6.20(m,2H)、6.11(d,1H)).
1H-NMR(400MHz,CDCl3):δ=8.72(d,1H)、8.58(d,1H)、7.65-7.75(m,3H)、7.53-7.61(m,2H)、7.47(m,2H)、7.38(t,1H)、7.34(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.66(d,1H)、8.59(d,1H)、7.70(m,3H)、7.62(t,1H)、7.42-7.54(m,3H)、7.37(m,3H)、7.32(d,1H)、7.27(m,1H)、6.80(d,1H)、6.51(d,1H).
1H-NMR(400MHz,CDCl3):δ=8.01(dd,2H)、7.56(t,1H)、7.52(dd,2H)、7.32(m,2H)、7.15(m,2H).
1H-NMR(400MHz,CDCl3):δ=8.0(m,2H)、7.56(t,1H)、7.35-7.42(m,4H)、7.15(m,2H).
1H NMR(δppm in CDCl3); 8.16 (dd, JHP = 13.2 Hz, J = 7.4 Hz, 4H), 7.61 (dd, J = 7.4, 8.0 Hz, 4H), 7.53 (dd, JHP = 6.2 Hz, J = 8.0 Hz, 4H), 7.42 (t, J = 7.4 Hz, 4H).
LRMS (DART) m/z 567 ([M+H]+)
1H NMR(δppm in CDCl3); 8.37 (d, J = 2.0 Hz, 4H), 7.54 (d, J = 8.4 Hz, 4H), 7.48 (dd, J = 2.0 Hz, 8.4 Hz, 4H), 2.78 (t, J = 7.6 Hz, 8H), 1.77 (m, 8H), 1.50 (sex, J = 7.3 Hz, 8H)、1.03 (t, J = 7.3 Hz, 12H).
LRMS (DART) m/z 686 (M+)
1H-NMR(δppm in CDCl3);10.03 (s, 1H), 8.93 (d, 2H), 7.82 (t, 2H), 7.76 (t, 2H), 7.61 (d, 2H), 7.51 (t, 2H), 7.33 (d, 2H), 7.28 (d, 2H), 2.84 (s, 3H).
LRMS(DART) calcd for C31H18B2O4 [(M + H)+] : 477.1, found : 477.2
1H-NMR(400MHz,CDCl3):δ = 2.27 (s, 6H), 2.39 (s, 6H),2.50 (s, 6H), 5.48 (brs, 2H), 6.68 (d, 2H), 6.83 (ddd, 4H), 6.89 (ddd, 4H), 7.07 (ddd, 4H), 7.17 (dd, 2H), 7.25 (ddd, 4H), 8.68 (sd, 2H).
13C-NMR(101MHz,CDCl3):δ = 20.78 (2C), 21.06 (2C), 21.11 (2C), 96.5 (2C), 116.7 (2C), 126.0 (4C), 128.2 (2C), 129.3 (4C), 129.9 (4C), 131.1 (4C), 131.3 (2C), 133.0 (2C), 134.6 (2C), 137.6 (2C), 139.8 (2C), 143.9 (2C), 145.9 (2C), 148.0 (2C), 151.0.
9,11-ジフェニル-4b,11,15b,19b-テトラヒドロ-9H-9,11,19b-トリアザ-4b,15b-ジボラベンゾ[3,4]フェナントロ[2,1,10,9-fghi]ペンタセンの合成
1H-NMR(400MHz,CDCl3):δ = 5.24 (s, 1H), 6.81 (d, 2H), 7.12 - 7.18 (m, 6H), 7.34 (td, 2H), 7.41 - 7.49 (m, 8H), 7.45 (ddd, 2H), 8.31 (dd, 2H), 8.81 (dd, 2H), 8.91 (dd, 2H).
HRMS (DART) m/z [M+H]+ Calcd for C42H28B2N3596.2483, observed 596.2499.
3,6,14,17-テトラメチル-9,11-ジ-p-トリル-4b,11,15b,19b-テトラヒドロ-9H-9,11,19b-トリアザ-4b,15b-ジボラベンゾ[3,4]フェナントロ[2,1,10,9-fghi]ペンタセンの合成
1H-NMR(400MHz,CDCl3):δ = 2.45 (s, 6H), 2.65 (s, 6H), 2.58 (s, 6H), 5.24 (brs, 1H), 6.74 (d, 2H), 6.97 (d, 4H), 7.15 - 7.27 (m, 6H), 7.34 (dd, 2H), 8.18 (d, 2H), 8.58 (d, 2H), 8.68 (d, 2H).
HRMS (DART) m/z [M+H]+ Calcd for C48H40B2N3680.3424, observed 680.3404.
1H-NMR(δppm in CDCl3);δ = 8.67 (dd, 2H), 7.68 (ddd, 2H), 7.50 - 7.66 (m, 4H), 7.38 (ddd, 2H), 7.25 (td, 1H), 7.19 (dd, 2H), 7.19 (S, 2H).
LRMS (DART) calcd for C24H16B1O3 [(M + H)+] : 363.1, found : 363.1
NMR測定により得られた化合物の構造を確認した。
1H-NMR(δppm in CDCl3);δ = 7.21 (t, 2H), 7.15 (t, 1H), 6.93 (d, 2H), 6.80-6.88 (m, 5H), 6.74 (s, 1H), 6.73 (d, 1H), 6.36 (s, 2H), 2.33 (s, 6H), 2.28 (s, 3H).
1H-NMR(δppm in CDCl3);δ = 8.51 (d, 2H), 7.26-7.33 (m, 3H), 7.18 (d, 2H), 6.97-7.06 (m, 3H), 6.76 (s, 2H), 2.50 (s, 6H), 2.39 (s, 3H).
LRMS(EI+) m/z 404 (M+)
NMR測定により得られた化合物の構造を確認した。
1H-NMR(δppm in CDCl3);δ = 7.16 (d, 4H), 7.11 (t, 1H), 6.95 (d, 4H), 6.63 (d, 2H), 2.60 (t, 4H), 1.60 (m, 4H), 1.36 (m, 4H), 0.93 (t, 6H).
1H-NMR(δppm in CDCl3);δ = 8.46 (s, 2H), 7.76 (t, 1H), 7.54 (d, 2H), 7.47 (d, 2H), 7.19 (d, 2H), 2.82 (t, 4H), 1.75 (m, 4H), 1.46 (m, 4H), 1.00 (t, 6H).
LRMS(EI+) m/z 382 (M+)
<化合物(1-176)を発光層のドーパント材料に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HIを入れたモリブデン製蒸着用ボート、HAT-CNを入れたモリブデン製蒸着ボート、HTを入れたモリブデン製蒸着用ボート、BH1を入れたモリブデン製蒸着用ボート、本発明の化合物(1-176)を入れたモリブデン製蒸着用ボート、ET-2を入れたモリブデン製蒸着用ボート、ET-1を入れたモリブデン製蒸着用ボート、LiFを入れたモリブデン製蒸着用ボートおよびアルミニウムを入れたタングステン製蒸着用ボートを装着した。
<化合物(1-100)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-176)を化合物(1-100)に替えた以外は実施例1に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約457nmにピークトップを有する青色発光が得られた。輝度100cd/m2における外部量子効率は2.78%であった。
<化合物(1-141)を発光層のドーパント材料に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HAT-CNを入れたモリブデン製蒸着用ボート、TBBを入れたモリブデン製蒸着用ボート、CBPを入れたモリブデン製蒸着ボート、本発明の化合物(1-141)を入れたモリブデン製蒸着用ボート、TPBiを入れたモリブデン製蒸着用ボート、LiFを入れたモリブデン製蒸着用ボートおよびアルミニウムを入れたタングステン製蒸着用ボートを装着した。
<化合物(1-81)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-141)を化合物(1-81)に替えた以外は実施例3に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度100cd/m2における外部量子効率は8.37%であった。
<化合物(1-91)を発光層のホスト材料に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HAT-CNを入れたモリブデン製蒸着用ボート、TBBを入れたモリブデン製蒸着用ボート、本発明の化合物(1-91)を入れたモリブデン製蒸着ボート、Ir(PPy)3を入れたモリブデン製蒸着用ボート、TPBiを入れたモリブデン製蒸着用ボート、LiFを入れたモリブデン製蒸着用ボートおよびアルミニウムを入れたタングステン製蒸着用ボートを装着した。
<化合物(1-152)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-152)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は9.36%であった。また、輝度100cd/m2における外部量子効率は13.26%であった。
<化合物(1-1048)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-1048)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は9.50%であった。また、輝度100cd/m2における外部量子効率は12.43%であった。
<化合物(1-1049)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-1049)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は6.54%であった。また、輝度100cd/m2における外部量子効率は7.44%であった。
<化合物(1-1050)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-1050)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は10.98%であった。また、輝度100cd/m2における外部量子効率は12.32%であった。
<化合物(1-100)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-100)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は5.73%であった。また、輝度100cd/m2における外部量子効率は8.75%であった。
<化合物(1-49)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-49)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は7.33%であった。また、輝度100cd/m2における外部量子効率は10.36%であった。
<化合物(1-176)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-176)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は10.74%であった。また、輝度100cd/m2における外部量子効率は11.77%であった。
<化合物(1-1069)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-1069)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は8.96%であった。また、輝度100cd/m2における外部量子効率は11.80%であった。
<化合物(1-1201)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-91)を化合物(1-1201)に替えた以外は実施例5に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は10.14%であった。また、輝度100cd/m2における外部量子効率は12.17%であった。
<化合物(1-1145)を発光層のドーパント材料に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HIを入れたモリブデン製蒸着用ボート、HAT-CNを入れたモリブデン製蒸着ボート、HTを入れたモリブデン製蒸着用ボート、BH1を入れたモリブデン製蒸着用ボート、本発明の化合物(1-1145)を入れたモリブデン製蒸着用ボート、ET-2を入れたモリブデン製蒸着用ボート、ET-1を入れたモリブデン製蒸着用ボート、LiFを入れたモリブデン製蒸着用ボートおよびアルミニウムを入れたタングステン製蒸着用ボートを装着した。
<化合物(1-401)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-1145)を化合物(1-401)に替えた以外は実施例15に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約458nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は4.33%であった。
<化合物(1-1101)を発光層のホスト材料に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HAT-CNを入れたタンタル製蒸着ルツボ、TBBを入れたタンタル製蒸着用ルツボ、TcTaを入れたタンタル製蒸着用ルツボ、本発明の化合物(1-1101)を入れたタンタル製蒸着用ルツボ、Ir(PPy)3を入れたタンタル製蒸着用ルツボ、TPBiを入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-1102)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-1101)を化合物(1-1102)に替えた以外は実施例17に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は7.99%だった。
<化合物(1-1103)を発光層のホスト材料に用いた素子>
発光層のホスト材料である化合物(1-1101)を化合物(1-1103)に替えた以外は実施例17に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は9.05%だった。
<化合物(1-1192)を電子輸送層に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HAT-CNを入れたタンタル製蒸着用ルツボ、TBBを入れたタンタル製蒸着用ルツボ、TcTaを入れたタンタル製蒸着用ルツボ、CBPを入れたタンタル製蒸着用ルツボ、Ir(PPy)3を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-1192)を入れたタンタル製蒸着用ルツボ、ET-3を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-1192)を電子輸送層1、ET-3を電子輸送層2に用いた素子>
電子輸送層1として化合物(1-1192)を10nm蒸着した後、電子輸送層2としてET-3を40nm蒸着することで電子輸送層を2層に替えた以外は実施例20に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約512nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は11.54%だった。
<化合物(1-447)を発光層のドーパントに用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HIを入れたタンタル製蒸着ルツボ、HAT-CNを入れたタンタル製蒸着用ルツボ、HTを入れたタンタル製蒸着用ルツボ、BH2を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-447)を入れたタンタル製蒸着用ルツボ、ET-4を入れたタンタル製蒸着用ルツボ、ET-3を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-50)を電子輸送層1/ET-1を電子輸送層2に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HIを入れたタンタル製蒸着用ルツボ、HAT-CNを入れたタンタル製蒸着用ルツボ、HTを入れたタンタル製蒸着用ルツボ、BH1を入れたタンタル製蒸着用ルツボ、BD1を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-50)を入れたタンタル製蒸着用ルツボ、ET-1を入れたタンタル製蒸着用ルツボ、ET-3を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-49)を電子輸送層1、ET-1を電子輸送層2に用いた素子>
電子輸送層1を化合物(1-49)に替えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は8.86%だった。
<化合物(1-50)を電子輸送層1、ET-3を電子輸送層2に用いた素子>
電子輸送層2をET-3に替えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は8.16%だった。
<化合物(1-49)を電子輸送層1、ET-3を電子輸送層2に用いた素子>
電子輸送層1を化合物(1-49)、電子輸送層2をET-3に替えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は8.94%だった。
<化合物(1-50)を電子輸送層1に用いた素子>
電子輸送層2をなくして、電子輸送層1の膜厚を30nmに変えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は4.63%だった。
<化合物(1-1050)を電子輸送層1に用いた素子>
電子輸送層2をなくして、電子輸送層1の膜厚を30nmに変えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は3.39%だった。
<化合物(1-1102)を電子輸送層1に用いた素子>
電子輸送層2をなくして、電子輸送層1の膜厚を30nmに変えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は4.54%だった。
<化合物(1-1050)を電子輸送層1、ET-1を電子輸送層2に用いた素子>
電子輸送層1を化合物(1-1050)に替えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は7.88%だった。
<化合物(1-1102)を電子輸送層1、ET-1を電子輸送層2に用いた素子>
電子輸送層1を化合物(1-1102)に替えた以外は実施例23に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は8.54%だった。
<化合物(1-422)を発光層のドーパントに、化合物(1-49)を電子輸送層に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HIを入れたタンタル製蒸着ルツボ、HAT-CNを入れたタンタル製蒸着用ルツボ、HTを入れたタンタル製蒸着用ルツボ、BH1を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-422)を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-49)を入れたタンタル製蒸着用ルツボ、ET-1を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-1152)を発光層のドーパント材料に、化合物(1-49)を電子輸送層に用いた素子>
発光層のドーパント材料である化合物(1-422)を化合物(1-1152)に替えた以外は実施例32に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約465nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.127,0.099)であり、輝度1000cd/m2における外部量子効率は5.47%であった。
<化合物(1-1159)を発光層のドーパント材料に、化合物(1-49)を電子輸送層に用いた素子>
発光層のドーパント材料である化合物(1-422)を化合物(1-1159)に替えた以外は実施例32に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.140,0.057)であり、輝度1000cd/m2における外部量子効率は6.92%であった。
<化合物(1-79)を発光層のドーパントに用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HIを入れたタンタル製蒸着ルツボ、HAT-CNを入れたタンタル製蒸着用ルツボ、HTを入れたタンタル製蒸着用ルツボ、BH1を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-79)を入れたタンタル製蒸着用ルツボ、ET-5を入れたタンタル製蒸着用ルツボ、ET-6を入れたタンタル製蒸着用ルツボ、Liqを入れた窒化アルミニウム製蒸着用ルツボ、マグネシウムを入れた窒化アルミニウム製ルツボおよび銀を入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-2305)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2305)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約459nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.142,0.113)であり、輝度1000cd/m2における外部量子効率は4.50%であった。
<化合物(1-2680)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2680)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約455nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.142,0.051)であり、輝度1000cd/m2における外部量子効率は6.14%であった。
<化合物(1-2679)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2679)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約463nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.129,0.084)であり、輝度1000cd/m2における外部量子効率は6.42%であった。
<化合物(1-422)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-422)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約464nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.127,0.094)であり、輝度1000cd/m2における外部量子効率は5.66%であった。
<化合物(1-447)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-447)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約449nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.148,0.041)であり、輝度1000cd/m2における外部量子効率は4.49%であった。
<化合物(1-1145)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-1145)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約451nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.146,0.059)であり、輝度1000cd/m2における外部量子効率は6.50%であった。
<化合物(1-1104)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-1104)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約462nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.145,0.144)であり、輝度1000cd/m2における外部量子効率は2.75%であった。
<化合物(1-142)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-142)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約470nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.140,0.196)であり、輝度1000cd/m2における外部量子効率は3.85%であった。
<化合物(1-2681)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2681)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約465nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.127,0.091)であり、輝度1000cd/m2における外部量子効率は5.25%であった。
<化合物(1-2682)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2682)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約457nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.139,0.059)であり、輝度1000cd/m2における外部量子効率は5.83%であった。
<化合物(1-422)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-422)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約478nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.096,0.184)であり、輝度1000cd/m2における外部量子効率は5.53%であった。
<化合物(1-1210)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-1210)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約439nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.155,0.029)であり、輝度1000cd/m2における外部量子効率は4.38%であった。
<化合物(1-1201)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-1201)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約439nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.153,0.042)であり、輝度1000cd/m2における外部量子効率は3.67%であった。
<化合物(1-2626)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2626)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約462nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.131,0.078)であり、輝度1000cd/m2における外部量子効率は5.66%であった。
<化合物(1-2683)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2683)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.140,0.057)であり、輝度1000cd/m2における外部量子効率は5.64%であった。
<化合物(1-2657)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2657)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約466nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.124,0.125)であり、輝度1000cd/m2における外部量子効率は5.28%であった。
<化合物(1-2699)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2699)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約459nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.133,0.091)であり、輝度1000cd/m2における外部量子効率は5.18%であった。
<化合物(1-2676)を発光層のドーパント材料に用いた素子>
発光層のドーパント材料である化合物(1-79)を化合物(1-2676)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約459nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.124,0.111)であり、輝度1000cd/m2における外部量子効率は6.82%であった。
<比較化合物1を発光層のドーパント材料に用いた素子>
比較化合物1は、国際公開第2012/118164号公報の63頁に化合物1として開示されている。発光層のドーパント材料である化合物(1-79)を(比較化合物1)に替えた以外は実施例35に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約471nmにピークトップを有する青色発光が得られた。その時のCIE色度は(x,y)=(0.145,0.170)であり、輝度1000cd/m2における外部量子効率は3.67%であった。
<化合物(1-3588)を電子輸送層1に用いた燐光発光素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HAT-CNを入れたタンタル製蒸着用ルツボ、TBBを入れたタンタル製蒸着用ルツボ、TcTaを入れたタンタル製蒸着用ルツボ、CBPを入れたタンタル製蒸着用ルツボ、Ir(PPy)3を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-3588)を入れたタンタル製蒸着用ルツボ、ET-1を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-1192)を電子輸送層1に用いた燐光発光素子>
電子輸送層1である化合物(1-3588)を化合物(1-1192)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は11.08%であった。
<化合物(1-3824)を電子輸送層1に用いた燐光発光素子>
電子輸送層1である化合物(1-3588)を化合物(1-3824)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は14.75%であった。
<化合物(1-3806)を電子輸送層1に用いた燐光発光素子>
電子輸送層1である化合物(1-3588)を化合物(1-3806)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は14.06%であった。
<化合物(1-601)を電子輸送層1に用いた燐光発光素子>
電子輸送層1である化合物(1-3588)を化合物(1-601)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は11.50%であった。
<化合物(1-152)を発光層のホスト、化合物(1-601)を電子輸送層1に用いた燐光発光素子>
発光層のホストであるCBPを化合物(1-152)、電子輸送層1である化合物(1-3588)を化合物(1-601)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は17.24%であった。
<化合物(1-49)を電子輸送層2に用いた燐光発光素子>
電子輸送層1である化合物(1-3588)を化合物(1-49)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は12.63%であった。
<化合物(1-152)を発光層のホスト、化合物(1-49)を電子輸送層1に用いた燐光発光素子>
発光層のホストであるCBPを化合物(1-152)、電子輸送層1である化合物(1-3588)を化合物(1-49)に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は12.55%であった。
<比較化合物1を電子輸送層1に用いた燐光発光素子>
電子輸送層1である化合物(1-3588)を比較化合物1に替えた以外は実施例54に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約510nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は7.50%であった。
<化合物(1-152)を発光層のホスト材料に用いたTADF(熱活性化遅延蛍光)有機EL素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HAT-CNを入れたタンタル製蒸着用ルツボ、TBBを入れたタンタル製蒸着用ルツボ、TcTaを入れたタンタル製蒸着用ルツボ、本発明の化合物(1-152)を入れたタンタル製蒸着用ルツボ、4CzIPNを入れたタンタル製蒸着用ルツボ、T2Tを入れたタンタル製蒸着用ルツボ、ET-1を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-152)を発光層のホスト材料に、化合物(1-49)を電子輸送層1に用いたTADF(熱活性化遅延蛍光)有機EL素子>
電子輸送層1であるT2Tを化合物(1-49)に替えた以外は実施例62に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約508nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は13.25%であった。
<化合物(1-152)を発光層のホスト材料に用いたTADF(熱活性化遅延蛍光)有機EL素子>
電子輸送層1であるT2TをET-5に替えた以外は実施例62に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約508nmにピークトップを有する緑色発光が得られた。輝度1000cd/m2における外部量子効率は11.5%であった。
<化合物(1-81)を発光層のドーパント材料に用いたTADF有機EL素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HAT-CNを入れたモリブデン製蒸着用ボート、TBBを入れたモリブデン製蒸着用ボート、TcTaを入れたモリブデン製蒸着ボート、mCPを入れたモリブデン製蒸着ボート、本発明の化合物(1-81)を入れたモリブデン製蒸着用ボート、TPBiを入れたモリブデン製蒸着用ボート、LiFを入れたモリブデン製蒸着用ボートおよびアルミニウムを入れたタングステン製蒸着用ボートを装着した。
<化合物(1-3824)を電子輸送層1に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HIを入れたタンタル製蒸着ルツボ、HAT-CNを入れたタンタル製蒸着用ルツボ、HTを入れたタンタル製蒸着用ルツボ、BH1を入れたタンタル製蒸着用ルツボ、BD1を入れたタンタル製蒸着用ルツボ、本発明の化合物(1-3824)を入れたタンタル製蒸着用ルツボ、ET-1を入れたタンタル製蒸着用ルツボ、LiFを入れたタンタル製蒸着用ルツボおよびアルミニウムを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-3806)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3824)を化合物(1-3806)に替えた以外は実施例66に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約455nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は4.84%であった。
<化合物(1-601)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3824)を化合物(1-601)に替えた以外は実施例66に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約455nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は6.47%であった。
<化合物(1-701)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3824)を化合物(1-701)に替えた以外は実施例66に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約455nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は6.55%であった。
<化合物(1-3690)を電子輸送層1に用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HIを入れたタンタル製蒸着ルツボ、HAT-CNを入れたタンタル製蒸着用ルツボ、HTを入れたタンタル製蒸着用ルツボ、BH1を入れたタンタル製蒸着用ルツボ、BD1を入れタンタル製蒸着用ルツボ、本発明の化合物(1-3690)を入れたタンタル製蒸着用ルツボ、ET-6を入れたタンタル製蒸着用ルツボ、Liqを入れた窒化アルミニウム製蒸着用ルツボ、マグネシウムを入れた窒化アルミニウム製ルツボおよび銀を入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1-1187)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-1187)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。
<化合物(1-1191)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-1191)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。
<化合物(1-1006)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-1006)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は6.68%であった。
<化合物(1-152-2)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-152-2)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は7.56%であった。
<化合物(1-601)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-601)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は5.78%であった。
<化合物(1-3654)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-3654)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。
<化合物(1-49)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-49)に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は6.73%であった。
<化合物(1-49)を電子輸送層1に用いた素子>
発光層のドーパント材料であるBD1をBD2に替えた以外は実施例77に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約454nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は6.10%であった。
<化合物(1-49)を電子輸送層1に用いた素子>
発光層のドーパント材料であるBD1をBD3に替えた以外は実施例77に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は6.28%であった。
<化合物(1-3588)を電子輸送層1に用いた素子>
電子輸送層1である化合物(1-3690)を化合物(1-3588)に、電子輸送層2であるET-6をET-7に替えた以外は実施例70に準じた方法で有機EL素子を得た。両電極に直流電圧を印加すると、約456nmにピークトップを有する青色発光が得られた。輝度1000cd/m2における外部量子効率は5.33%であった。
101 基板
102 陽極
103 正孔注入層
104 正孔輸送層
105 発光層
106 電子輸送層
107 電子注入層
108 陰極
Claims (24)
- 下記一般式(1)で表される多環芳香族化合物、または下記一般式(1)で表される構造を複数有する多環芳香族化合物の多量体。
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリールまたはアルキルであり、
X1およびX2は、それぞれ独立して、O、N-R、SまたはSeであり、前記N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは連結基または単結合により前記A環、B環および/またはC環と結合していてもよく、そして、
式(1)で表される化合物または構造における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい。) - A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換または無置換のアリール、置換または無置換のヘテロアリール、置換または無置換のジアリールアミノ、置換または無置換のジヘテロアリールアミノ、置換または無置換のアリールヘテロアリールアミノ、置換または無置換のアルキル、置換または無置換のアルコキシまたは置換または無置換のアリールオキシで置換されていてもよく、また、これらの環はY1、X1およびX2から構成される上記式中央の縮合2環構造と結合を共有する5員環または6員環を有し、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリールまたはアルキルであり、
X1およびX2は、それぞれ独立して、O、N-R、SまたはSeであり、前記N-RのRはアルキルで置換されていてもよいアリール、アルキルで置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは-O-、-S-、-C(-R)2-または単結合により前記A環、B環および/またはC環と結合していてもよく、前記-C(-R)2-のRは水素またはアルキルであり、
式(1)で表される化合物または構造における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよく、そして、
多量体の場合には、一般式(1)で表される構造を2または3個有する2または3量体である、
請求項1に記載する多環芳香族化合物またはその多量体。 - 下記一般式(2)で表される、請求項1に記載する多環芳香族化合物。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、また、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRは炭素数6~12のアリールまたは炭素数1~6のアルキルであり、
X1およびX2は、それぞれ独立して、O、N-R、SまたはSeであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルであり、また、前記N-RのRは-O-、-S-、-C(-R)2-または単結合により前記a環、b環および/またはc環と結合していてもよく、前記-C(-R)2-のRは炭素数1~6のアルキルであり、そして、
式(2)で表される化合物における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい。) - R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11は、それぞれ独立して、水素、炭素数6~30のアリール、炭素数2~30のヘテロアリールまたはジアリールアミノ(ただしアリールは炭素数6~12のアリール)であり、また、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共に炭素数9~16のアリール環または炭素数6~15のヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素は炭素数6~10のアリールで置換されていてもよく、
Y1は、B、P、P=O、P=SまたはSi-Rであり、前記Si-RのRは炭素数6~10のアリールまたは炭素数1~4のアルキルであり、
X1およびX2は、それぞれ独立して、O、N-RまたはSであり、前記N-RのRは炭素数6~10のアリールまたは炭素数1~4のアルキルであり、そして、
式(2)で表される化合物における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい、
請求項3に記載する多環芳香族化合物。 - 前記ハロゲンはフッ素である、請求項1~4のいずれかに記載する多環芳香族化合物またはその多量体。
- 下記式(1-21)、下記式(1-23)、下記式(1-24)、下記式(1-50)、下記式(1-152)、下記式(1-201)、下記式(1-401)、下記式(1-422)、下記式(1-1048)、下記式(1-1049)、下記式(1-1050)、下記式(1-1069)、下記式(1-1084)、下記式(1-1090)、下記式(1-1092)、下記式(1-1101)、下記式(1-1102)、下記式(1-1103)、下記式(1-1145)、下記式(1-1152)、下記式(1-1159)、下記式(1-1187)、下記式(1-1190)、下記式(1-1191)、下記式(1-1192)、下記式(1-1201)、下記式(1-1210)、下記式(1-1247)、下記式(1-1250)、下記式(1-1251)、下記式(1-1252)または下記式(1-1271)で表される、請求項1に記載する多環芳香族化合物。
- 下記式(1-1-1)、下記式(1-79)、下記式(1-142)、下記式(1-152-2)、下記式(1-158)、下記式(1-159)、下記式(1-721)、下記式(1-1006)、下記式(1-1104)、下記式(1-1149)、下記式(1-1150)、下記式(1-1301)、下記式(1-1351)、下記式(1-2305)、下記式(1-2626)、下記式(1-2657)、下記式(1-2662)、下記式(1-2665)、下記式(1-2676)、下記式(1-2678)、下記式(1-2679)、下記式(1-2680)、下記式(1-2681)、下記式(1-2682)、下記式(1-2683)、下記式(1-2691)、下記式(1-2699)、下記式(1-3588)、下記式(1-3654)、下記式(1-3690)、下記式(1-3806)、下記式(1-3824)、下記式(1-4114)、下記式(1-4150)、下記式(1-4341)、下記式(1-4346)、下記式(1-4401)、下記式(1-4421-1)で表される、請求項1に記載する多環芳香族化合物。
- 請求項1ないし8のいずれかに記載する多環芳香族化合物またはその多量体を含有する、有機デバイス用材料。
- 前記有機デバイス用材料が、有機電界発光素子用材料、有機電界効果トランジスタ用材料または有機薄膜太陽電池用材料である、請求項9に記載する有機デバイス用材料。
- 発光層用材料である、請求項10に記載する有機電界発光素子用材料。
- 電子注入層用材料または電子輸送層用材料である、請求項10に記載する有機電界発光素子用材料。
- 正孔注入層用材料または正孔輸送層用材料である、請求項10に記載する有機電界発光素子用材料。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置され、請求項11に記載する発光層用材料を含有する発光層とを有する、有機電界発光素子。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層と、前記陰極および前記発光層の間に配置され、請求項12に記載する電子注入層用材料および/または電子輸送層用材料を含有する電子注入層および/または電子輸送層とを有する、有機電界発光素子。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層と、前記陽極および前記発光層の間に配置され、請求項13に記載する正孔注入層用材料および/または正孔輸送層用材料を含有する正孔注入層および/または正孔輸送層とを有する、有機電界発光素子。
- さらに、前記陰極と該発光層との間に配置される電子輸送層および/または電子注入層を有し、該電子輸送層および電子注入層の少なくとも1つは、キノリノール系金属錯体、ピリジン誘導体、フェナントロリン誘導体、ボラン誘導体およびベンゾイミダゾール誘導体からなる群から選択される少なくとも1つを含有する、請求項14~16のいずれかに記載する有機電界発光素子。
- 前記電子輸送層および/または電子注入層が、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、請求項17に記載の有機電界発光素子。
- 請求項14~18のいずれかに記載する有機電界発光素子を備えた表示装置。
- 請求項14~18のいずれかに記載する有機電界発光素子を備えた照明装置。
- さらにルイス酸を加えて反応を促進させることを特徴とする、請求項21または22に記載する製造方法。
- さらに中間体におけるX1とX2の間の水素原子をあらかじめハロゲン化する反応工程を含む、請求項21~23のいずれかに記載する製造方法。
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Also Published As
Publication number | Publication date |
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KR101955648B1 (ko) | 2019-03-07 |
TWI636056B (zh) | 2018-09-21 |
TW201538513A (zh) | 2015-10-16 |
CN106905367B (zh) | 2020-11-17 |
EP3345911A1 (en) | 2018-07-11 |
KR20190025065A (ko) | 2019-03-08 |
JP5935199B2 (ja) | 2016-06-15 |
CN111662314B (zh) | 2021-10-26 |
KR101955647B1 (ko) | 2019-03-07 |
CN106905367A (zh) | 2017-06-30 |
CN111909189A (zh) | 2020-11-10 |
EP3109253A4 (en) | 2017-08-16 |
EP3109253B1 (en) | 2018-10-24 |
CN105431439B (zh) | 2020-09-25 |
CN105431439A (zh) | 2016-03-23 |
KR20160134881A (ko) | 2016-11-23 |
EP3345911B1 (en) | 2018-11-28 |
KR20160119683A (ko) | 2016-10-14 |
CN111662314A (zh) | 2020-09-15 |
JPWO2015102118A1 (ja) | 2017-03-23 |
KR20170122296A (ko) | 2017-11-03 |
KR20170121345A (ko) | 2017-11-01 |
CN111892615A (zh) | 2020-11-06 |
EP3109253A1 (en) | 2016-12-28 |
KR102058028B1 (ko) | 2019-12-20 |
KR101886773B1 (ko) | 2018-08-08 |
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