US2011049496A1PendingUtilityA1
Organic electroluminescence device
Est. expiryAug 31, 2029(~3 yrs left)· nominal 20-yr term from priority
Inventors:Eiji Fukuzaki
H05B 33/14C09K 2211/1044C09K 2211/1088C09K 11/06C09K 2211/1033C09K 2211/185C09K 2211/1029C07F 15/0033H10K 85/342H10K 85/344H10K 85/348H10K 2101/10H10K 85/346H10K 85/331H10K 85/631H10K 50/11H10K 85/324
50
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Claims
Abstract
An organic electroluminescence device material comprising a metal complex having a neopentyl group, for example, as shown below; and an organic electroluminescence device comprising a substrate having thereon a pair of electrodes and at least one organic layer between the electrodes, the organic layer containing a light emitting layer, wherein any one of the organic layer contains the organic electroluminescence device material.
Claims
exact text as granted — not AI-modified1 . An organic electroluminescence device material that is a compound represented by the following formula (3):
wherein M 31 represents iridium;
each of A31 and A32 independently represents a nitrogen atom or a carbon atom, each of R 33 to R 36 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
any combination selected from R 33 and R 34 , R 34 and R 35 , and R 35 and R 36 may combine with each other to form a benzene ring, and the benzene ring may have at least one substituent selected from a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, and a cyano group;
Z 32 represents an atomic group for forming a benzene ring, a pyrazole ring, a pyridine ring or a thiophene ring together with A31 and A32, and the benzene ring, pyrazole ring, pyridine ring or thiophene ring may have at least one substituent selected from a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, and a cyano group;
each of L 32 and L 33 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 31 represents an atomic group for forming a bidentate ligand represented by the following formula (l-1), (l-4), (l-10), (l-15), (l-16) or (l-17) together with L 32 and L 33 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 31 and S 32 represents a substituent shown by (a) below;
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4;
wherein each of Rx, Ry and Rz independently represents a hydrogen atom, an alkyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group.
2 . The organic electroluminescence device material as claimed in claim 1 , wherein the compound represented by formula (3) is represented by the following formula (4):
wherein M 41 represents iridium;
each of R 43 to R 46 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
any combination selected from R 43 and R 44 , R 44 and R 45 , and R 45 and R 46 may combine with each other to form a benzene ring, and the benzene ring may have at least one substituent selected from a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, and a cyano group;
each of B 41 to B 44 independently represents a nitrogen atom or C—R 47 , provided that two or more of B 41 to B 44 are not a nitrogen atom at the same time;
R 47 represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group, each R 47 may be the same as or different from every other R 47 ;
each of L 42 and L 43 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 41 represents an atomic group for forming a bidentate ligand represented by formula (l-1), (l-4), (l-10), (l-15), (l-16) or (l-17) together with L 42 and L 43 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 41 and S 42 represents a substituent shown by (a); and
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
3 . The organic electroluminescence device material as claimed in claim 2 ,
wherein the compound represented by formula (4) is represented by the following formula (5):
wherein M 51 represents iridium;
each of R 53 to R 510 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
any combination selected from R 53 and R 54 , R 54 and R 55 , and R 55 and R 56 may combine with each other to form a benzene ring, and the benzene ring may have at least one substituent selected from a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, and a cyano group:
each of L 52 and L 53 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 51 represents an atomic group for forming a bidentate ligand represented by formula (l-1), (l-4), (l-15), (l-16) or (l-17) together with L 52 and L 53 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 51 and S 52 represents a substituent shown by (a); and
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
4 . The organic electroluminescence device material as claimed in claim 3 ,
wherein the compound represented by formula (5) is represented by the following formula (5-4):
wherein M 541 represents iridium;
each of R 543 to R 5412 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
each of L 542 and L 543 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 541 represents an atomic group for forming a bidentate ligand represented by formula (l-1), (l-4), (l-10), (l-15), (l-16) or (l-17) together with L 542 and L 543 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 541 and S 542 represents a substituent shown by (a); and
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
5 . The organic electroluminescence device material as claimed in claim 3 ,
wherein the compound represented by formula (5) is represented by the following formula (5-7):
wherein M 571 represents iridium;
each of R 573 to R 5712 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
each of L 572 and L 573 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 571 represents an atomic group for forming a bidentate ligand represented by formula (l-1), (l-4), (l-10), (l-15), (l-16) or (l-17) together with L 572 and L 573 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 571 and S 572 represents a substituent shown by (a); and
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
6 . The organic electroluminescence device material as claimed in claim 2 ,
wherein the compound represented by formula (4) is represented by the following formula (6):
wherein M 61 represents iridium;
each of R 63 to R 66 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
each of B 61 to B 63 independently represents C—R 67 , R 67 represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
each R 67 may be the same as or different from every other R 67 ;
each of L 62 and L 63 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 61 represents an atomic group for forming a bidentate ligand represented by formula (l-1), (l-4), (l-10), (l-15), (l-16) or (l-17) together with L 62 and L 63 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 61 and S 62 represents a substituent shown by (a); and
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
7 . The organic electroluminescence device material as claimed in claim 1 ,
wherein the compound represented by formula (3) is represented by the following formula (7):
wherein M 71 represents iridium;
each of R 73 to R 76 independently represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, or a cyano group;
each of A71 and A72 independently represents a nitrogen atom or a carbon atom, each of D 71 to D 73 independently represents an atom selected from carbon, nitrogen and sulfur, provided that the 5-membered ring formed by D 71 to D 73 , A71 and A72 represents a pyrazole ring or a thiophene ring, and the bond between atoms in the 5-membered ring formed by D 71 to D 73 , A71 and A72 represents a single bond or a double bond;
each of D 71 to D 73 when these can be further substituted may have at least one substituent selected from a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a fluorine atom, an alkyl group-substitutable aryl group, and a cyano group;
each of L 72 and L 73 independently represents a carbon atom, a nitrogen atom, an oxygen atom or a phosphorus atom;
E 71 represents an atomic group for forming a bidentate ligand represented by formula (l-1), (l-4), (l-15), (l-16) or (l-17) together with L 72 and L 73 ;
k represents an integer of 1 to 3, l represents an integer of 0 to 2, k+1 is 3;
each of S 71 and S 72 represents a substituent shown by (a); and
each of n and m represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
8 . The organic electroluminescence device material as claimed in claim 1 ,
wherein each of R 33 to R 36 , R 43 to R 46 , R 53 to R 510 , R 543 to R 5412 , R 573 to R 5712 , R 63 to R 66 and R 73 to R 76 independently represents a methyl group, a fluorine atom or a phenyl group.
9 . The organic electroluminescence device material as claimed in claim 1 ,
wherein said bidentate ligand is represented by formula (l-1), (l-4) or (l-15).
10 . An organic electroluminescence device material represented by the following formula (13):
wherein each of A131 and A132 independently represents a nitrogen atom or a carbon atom;
each of Y 131 and Y 132 represents a single bond;
L 131 represents, together with X 131 and a carbon atom, a substituted or unsubstituted arylene group bonded to A131 through a carbon atom adjacent to the carbon atom bonded to X 131 ,
together with X 131 and a carbon atom, a substituted or unsubstituted pyridylene group bonded to A131 through a carbon atom adjacent to the carbon atom bonded to X 131 ,
together with X 131 and a carbon atom, a substituted or unsubstituted benzofurandiyl group bonded to A131 through a carbon atom adjacent to the carbon atom bonded to X 131 ,
together with X 131 and a carbon atom, a pyrazolediyl group bonded to A131 through a nitrogen atom adjacent to the carbon atom bonded to X 131 , or
together with X 131 and an oxygen atom, a carboxylato group bonded to A131 through a carbon atom adjacent to the carbon atom bonded to X 131 ;
L 132 represents, together with X 132 and a carbon atom, a substituted or unsubstituted arylene group bonded to A132 through a carbon atom adjacent to the carbon atom bonded to X 132 ,
together with X 132 and a carbon atom, a substituted or unsubstituted pyridylene group bonded to A132 through a carbon atom adjacent to the carbon atom bonded to X 132 ,
together with X 132 and a carbon atom, a substituted or unsubstituted benzofurandiyl group bonded to A132 through a carbon atom adjacent to the carbon atom bonded to X 132 ,
together with X 132 and a carbon atom, a pyrazolediyl group bonded to A132 through a nitrogen atom adjacent to the carbon atom bonded to X 132 , or
together with X 132 and an oxygen atom, a carboxylato group bonded to A132 through a carbon atom,
provided that the substituent in L 131 and L 132 is at least one group selected from a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom and a cyano group;
each of Z 131 and Z 132 independently represents a pyridine ring, an imidazole ring or a pyrazole ring, each of Z 131 and Z 132 may further have at least one substituent selected from a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom and a cyano group;
each of X 131 and X 132 independently represents an oxygen atom or a single bond;
E 131 represents a divalent linking group represented by —C(R 1 )(R 2 )—, each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 131 and S 132 represents a substituent shown by (a) below; and
each of n and m independently represents an integer of 0 to 4, and n+m is an integer of 1 to 4.
11 . The organic electroluminescence device material as claimed in claim 10 ,
wherein the compound represented by formula (13) is represented by the following formula (14):
wherein each of A141 to A146 independently represents a nitrogen atom or a carbon atom;
each of Z 141 and Z 142 independently represents a pyridine ring, an imidazole ring or a pyrazole ring, and may further have at least one substituent selected from a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom and a cyano group;
Z 143 represents an atomic group for forming an aryl group, a pyridyl group, a benzofuranyl group or a pyrazolyl group together with A142 and A143;
Z 144 represents an atomic group for forming an aryl group, a pyridyl group, a benzofuranyl group or a pyrazolyl group together with A145 and A146;
E 141 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group; and
each of S 141 to S 144 represents a substituent shown by (a), each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
12 . The organic electroluminescence device material as claimed in claim 11 ,
wherein the compound represented by formula (14) is represented by the following formula (15):
wherein each of A151 and A154 independently represents a nitrogen atom or a carbon atom;
each of R 153 to R 158 independently represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
Z 151 represents an atomic group for forming an aryl group, a pyridyl group, a benzofuranyl group or a pyrazolyl group together with A151 and A152;
Z 152 represents an atomic group for forming an aryl group, a pyridyl group, a benzofuranyl group or a pyrazolyl group together with A153 and A154;
E 151 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 151 to S 154 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
13 . The organic electroluminescence device material as claimed in claim 12 ,
wherein the compound represented by formula (15) is represented by the following formula (16):
wherein each of R 163 to R 168 independently represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
each of B 161 to B 168 independently represents a nitrogen atom or C—R 169 , provided that two or more of B 161 to B 164 are not a nitrogen atom at the same time and two or more of B 165 to B 168 are not a nitrogen atom at the same time;
R 169 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
each R 169 may be the same as or different from every other R 169 ;
E 161 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 161 to S 164 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
14 . The organic electroluminescence device material as claimed in claim 12 ,
wherein the compound represented by formula (15) is represented by the following formula (17):
wherein each of R 173 to R 178 independently represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
each of A171 and A173 represents a nitrogen atom;
each of A172 and A174 represents a carbon atom;
each of D 171 and D 174 represents a nitrogen atom;
each of D 172 , D 173 , D 175 and D 176 represents C—R 179 , R 179 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
E 171 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 171 to S 174 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
15 . The organic electroluminescence device material as claimed in claim 11 ,
wherein the compound represented by formula (14) is represented by the following formula (18):
wherein each of A181 to A186 independently represents a nitrogen atom or a carbon atom;
each of D 181 to D 184 represents a nitrogen atom or C—R 18 , R 18 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group, provided that each of the 5-membered rings formed by D 181 , D 182 , A181, the nitrogen atom and the carbon atom and by D 183 , D 184 , A184, the nitrogen atom and the carbon atom represents an imidazole ring or a pyrazole ring;
Z 181 represents an atomic group for forming an aryl group, a pyridyl group, a benzofuranyl group or a pyrazolyl group together with A182 and A183;
Z 182 represents an atomic group for forming an aryl group, a pyridyl group, a benzofuranyl group or a pyrazolyl group together with A185 and A186;
E 181 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 181 to S 184 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
16 . The organic electroluminescence device material as claimed in claim 11 ,
wherein the compound represented by formula (14) is a compound represented by the following formula (19):
wherein each of A191 and A192 independently represents a nitrogen atom or a carbon atom;
each of D 191 to D 194 represents a nitrogen atom or C—R 19 , R 19 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group, provided that each of the 5-membered rings formed by D 191 , D 192 , A191, the nitrogen atom and the carbon atom and by D 193 , D 194 , A194, the nitrogen atom and the carbon atom represents an imidazole ring or a pyrazole ring;
each of B 191 to B 198 independently represents a nitrogen atom or C—R 199 , provided that two or more of B 191 to B 194 are not a nitrogen atom at the same time and two or more of B 195 to B 198 are not a nitrogen atom at the same time;
R 199 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group, each R 199 may be the same as or different from every other R 199 ;
E 191 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 191 to S 194 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
17 . The organic electroluminescence device material as claimed in claim 16 ,
wherein the compound represented by formula (19) is represented by the following formula (20):
wherein each of R 203 to R 206 independently represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
each of B 201 to B 208 independently represents a nitrogen atom or C—R 207 , provided that two or more of B 201 to B 204 are not a nitrogen atom at the same time and two or more of B 205 to B 208 are not a nitrogen atom at the same time;
R 207 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group, each R 207 may be the same as or different from every other R 207 ;
E 201 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 201 to S 204 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
18 . The organic electroluminescence device material as claimed in claim 16 ,
wherein the compound represented by formula (19) is represented by the following formula (21):
wherein each of R 213 and R 214 independently represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
each of R 215 and R 216 independently represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group;
each of B 211 to B 218 independently represents a nitrogen atom or C—R 217 , provided that two or more of B 211 to B 214 are not a nitrogen atom at the same time and two or more of B 215 to B 218 are not a nitrogen atom at the same time;
R 217 represents a hydrogen atom, a methyl group, a tert-butyl group, a trifluoromethyl group, an alkyl group-substitutable aryl group, a fluorine atom, or a cyano group, each R 217 may be the same as or different from every other R 217 ;
R 211 represents a divalent linking group represented by —C(R 1 )(R 2 )—;
each of R 1 and R 2 independently represents an alkyl group or a phenyl group;
each of S 211 to S 214 represents a substituent shown by (a); and
each of n, m, k and l represents an integer of 0 to 4, and n+m+k+l is an integer of 1 to 4.
19 . A light emitting layer comprising at least one compound represented by formula (3) in claim 1 .
20 . An organic electroluminescence device comprising:
a substrate; a pair of electrodes on the substrate; and at least one organic containing a light emitting layer between the electrodes, wherein the organic layer contains the organic electroluminescence device material of claim 1 .
21 . The organic electroluminescence device as claimed in claim 20 ,
wherein at least one compound represented by formula (3) is contained in the light emitting layer.
22 . The organic electroluminescence device as claimed in claim 20 ,
wherein a carbazole or indole structure-containing material is further contained in any one of the organic layer.
23 . The organic electroluminescence device as claimed in claim 20 ,
wherein a carbazole or indole structure-containing material is further contained in the light emitting layer.
24 . The organic electroluminescence device as claimed in claim 20 ,
wherein the maximum luminescence wavelength is from 400 to 465 nm.
25 . The organic electroluminescence device as claimed in claim 20 ,
wherein the content of the organic electroluminescence device material in the light emitting layer is from 5 to 30 mass %.
26 . The organic electroluminescence device as claimed in claim 20 ,
wherein at least one layer of the organic layer is formed by a wet process.
27 . A display apparatus using the organic electroluminescence device of claim 20 .
28 . An illumination apparatus using the organic electroluminescence device claimed in of claim 20 .Join the waitlist — get patent alerts
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