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US 9,871,206 B2Granted
Compound, organic electroluminescence device material, organic electroluminescence device and electronic device
AssigneeIdemitsu Kosan Co., Ltd.
InventorsSayaka Mizutani, Takayasu Sado
Life of this patent
Estimating the term…
Abstract
A compound is represented by a formula (1) below. In the formula (1), X1 to X8 each independently represent a carbon atom to be bonded to a group represented by the following formula (20), CRX or a nitrogen atom. At least one of X1 to X8 is a carbon atom to be bonded to the group represented by the following formula (2). RX is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or the like.
Claims51
A compound represented by formula (1),
- where:
- X1 to X8 each independently represent a carbon atom bonded to a group represented by formula (2), CRX, or a nitrogen atom;
- at least one of X1 to X8 is a carbon atom bonded to a group represented by formula (2);
- each RX is independently selected from the group consisting of:
- a hydrogen atom,
- a halogen atom,
- a cyano group,
- a nitro group,
- a substituted or unsubstituted hydroxyl group,
- a substituted or unsubstituted carboxyl group,
- a substituted or unsubstituted sulfonyl group,
- a substituted or unsubstituted boryl group,
- a substituted or unsubstituted phosphino group,
- a substituted or unsubstituted mercapto group,
- a substituted or unsubstituted acyl group,
- a substituted or unsubstituted amino group,
- a substituted or unsubstituted silyl group,
- a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and
- a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;
- and
- among X1 to X8, adjacent RX of CRX are bonded to each other to form a cyclic structure, or are not bonded to each other;
- where:
- b is an integer of 1 to 5;
- c is an integer of 1 to 8;
- Z is an oxygen atom, a sulfur atom or a silicon atom;
- when b is 2 to 5, plural Z are the same or different;
- when Z is a silicon atom, R9 and R10 are bonded to the silicon atom, R9 and R10 each independently represent RX as defined in formula (1), and R9 and R10 are optionally bonded to the structure represented by formula (1);
- when Z is a silicon atom, R9 and R10 are not bonded to each other to form a cyclic structure;
- L is a single bond or a linking group;
- the linking group is a substituted or unsubstituted, linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted polyvalent aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted polyvalent heteroaryl group having 5 to 40 ring atoms;
- the polyvalent heteroaryl group having 5 to 40 ring atoms for L is a group selected from
- a substituted or unsubstituted polyvalent group derived from a phenanthroline ring represented by formula (1), a pyrroyl group, a pyrazinyl group, a pyridinyl group, an indolyl group, an isoindolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a carbazolyl group, a phenanthrydinyl group, a phenanthrolinyl group, a thienyl group, and a group formed based on a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, a benzo[c]dibenzofuran ring, or a silafluorene ring;
- when c is 2 to 8, plural L are the same or different;
- Y1 to Y8 each independently represent a nitrogen atom, CRY, or a carbon atom bonded to L;
- each RY is a hydrogen atom;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), h is 1, Z is an oxygen atom, Y4 or Y5 is a carbon atom bonded to L, and c is 2, the L closer to the phenanthroline ring represented by formula (1) is a divalent group other than an anthracene group;
- when two of X1 to X8 are carbon atoms bonded to the group represented by formula (2), b and c are 1, both of Z are sulfur atoms, Y4 or Y5 is a carbon atom bonded to L, and L is a p-phenylene group, L is bonded to any one of X1, X2, X4, X5, X7 and X8;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y3 is a carbon atom bonded to L, and L is a p-phenylene group, Y4 is CRY, RY being a group other than a phenyl group;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y6 is a carbon atom bonded to L, and L is a p-phenylene group, Y5 is CRY, RY being a group other than a phenyl group;
- when X4 or X5 is a carbon atom bonded to the group represented by formula (2), Y2 is a carbon atom bonded to L, L is a single bond, and Z is an oxygen atom, Y7 is CRY, RY being a group other than a pyrenyl group;
- and
- when X4 or X5 is a carbon atom bonded to the group represented by formula (2), Y7 is a carbon atom bonded to L, L is a single bond, and Z is an oxygen atom, Y2 is CRY, RY being a group other than a pyrenyl group.
43 more elements
A compound represented by the following formula (1),
- where:
- X1 to X8 each independently represent a carbon atom bonded to a group represented by the following formula (2), CRX or a nitrogen atom;
- two or more of X1 to X8 are carbon atoms bonded to a group represented by formula (2);
- each RX is independently selected from the group consisting of:
- a hydrogen atom,
- a halogen atom,
- a cyano group,
- a nitro group,
- a substituted or unsubstituted hydroxyl group,
- a substituted or unsubstituted carboxyl group,
- a substituted or unsubstituted sulfonyl group,
- a substituted or unsubstituted boryl group,
- a substituted or unsubstituted phosphino group,
- a substituted or unsubstituted mercapto group,
- a substituted or unsubstituted acyl group,
- a substituted or unsubstituted amino group,
- a substituted or unsubstituted silyl group,
- a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and
- a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;
- and
- among X1 to X8, adjacent RX of CRX are bonded to each other to form a cyclic structure, or are not bonded to each other;
- where:
- b is an integer of 1 to 5;
- c is an integer of 1 to 8;
- Z is an oxygen atom;
- a sulfur atom or a silicon atom;
- when b is 2 to 5, plural Z are the same or different;
- when Z is a silicon atom, R9 and R10 are bonded to the silicon atom, R9 and R10 each independently represent RX as defined in formula (1), and R9 and R10 are optionally bonded to the structure represented by formula (1);
- when Z is a silicon atom, R9 and R10 are not bonded to each other to form a cyclic structure;
- L is a single bond or a linking group;
- the linking group is a substituted, or unsubstituted, linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted polyvalent aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted polyvalent heteroaryl group having 5 to 40 ring atoms;
- the polyvalent heteroaryl group having 5 to 40 ring atoms for L is a group selected from a substituted or unsubstituted polyvalent group derived from a phenanthroline ring represented by formula (1), a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group, an isoindolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a carbazolyl group, a phenanthrydinyl group, a phenanthrolinyl group, a thienyl group, and a group based on a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, a benzo[c]dibenzofuran ring, or a silafluorene ring;
- when c is 2 to 8, plural L are the same or different;
- Y1 to Y8 each independently represent a nitrogen atom, CRY, or a carbon atom bonded to L;
- each RY is independently selected from the group consisting of:
- a hydrogen atom,
- a halogen atom,
- a cyano group,
- a nitro group,
- a substituted or unsubstituted hydroxyl group,
- a substituted or unsubstituted carboxyl group,
- a substituted or unsubstituted sulfonyl group,
- a substituted or unsubstituted boryl group,
- a substituted or unsubstituted phosphino group,
- a substituted or unsubstituted mercapto group,
- a substituted or unsubstituted acyl group,
- a substituted or unsubstituted amino group,
- a substituted or unsubstituted silyl group,
- a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and
- a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;
- the heteroaryl group having 5 to 40 ring atoms for RY comprises a substituted or unsubstituted phenanthrolyl group derived from the phenanthroline ring represented by formula (1);
- adjacent RY are bonded to each other to form a cyclic structure, or are not bonded to each other;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b is 1, Z is an oxygen atom, Y4 or Y5 is a carbon atom bonded to L, and c is 2, the L closer to the phenanthroline ring represented by formula (1) is a divalent group other than an anthracene group;
- when two of X1 to X8 are carbon atoms bonded to the group represented by formula (2), b and c are 1, both of Z are sulfur atoms, Y4 or Y5 is a carbon atom bonded to L, and L is a p-phenylene group, L is bonded to any one of X1, X2, X4, X5, X7 and X8;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y3 is a carbon atom bonded to L, and L is a p-phenylene group, Y4 is CRY, RY being a group other than a phenyl group;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y6 is a carbon atom bonded to L, and L is a p-phenylene group, Y5 is CRY, RY being a group other than a phenyl group;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), Z is a silicon atom, Y3 is a carbon atom bonded to L, L is a single bond, and Y6 is CRY, RY being the phenanthrolyl group of the heteroaryl group having 5 to 40 ring atoms in CRY for Y6, RY bonds to C at a position other than position 2 of the phenanthrolyl group;
- when X4 or X5 is a carbon atom bonded to the group represented by formula (2), Y2 is a carbon atom bonded to L, L is a single bond, and Z is an oxygen atom, Y7 is CRY, RY being a group other than a pyrenyl group;
- and
- when X4 or X5 is a carbon atom bonded to the group represented by formula (2), Y7 is a carbon atom bonded to L, L is a single bond, and Z is an oxygen atom, Y2 is CRY, RY being a group other than a pyrenyl group.
65 more elements
A compound represented by the following formula (1-1),
- where:
- A2 and A3 each independently represent a structure represented by formula (1);
- c1 is an integer of 1 to 8;
- c2 is an integer of 1 to 8;
- L1 and L2 each independently represent a single bond or a linking group;
- the linking group is a substituted or unsubstituted, linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 30 carbon atoms,
- a substituted or unsubstituted polyvalent aryl group having 6 to 40 ring carbon atoms, or
- a substituted or unsubstituted polyvalent heteroaryl group having 5 to 40 ring atoms;
- the polyvalent heteroaryl group having 5 to 40 ring atoms for L1 and L2 comprises a substituted or unsubstituted polyvalent group derived from a phenanthroline ring represented by formula (1);
- when c is 2 to 8, plural L1 and L2 are the same or different;
- Y1 to Y8 each independently represent a nitrogen atom, CRY, or a carbon atom bonded to L1 or L2;
- each RY is each independently selected from the group consisting of
- a hydrogen atom,
- a halogen atom,
- a cyano group,
- a nitro group,
- a substituted or unsubstituted hydroxyl group,
- a substituted or unsubstituted carboxyl group,
- a substituted or unsubstituted sulfonyl group,
- a substituted or unsubstituted boryl group,
- a substituted or unsubstituted phosphino group,
- a substituted or unsubstituted mercapto group,
- a substituted or unsubstituted acyl group,
- a substituted or unsubstituted amino group,
- a substituted or unsubstituted silyl group,
- a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and
- a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;
- the heteroaryl group having 5 to 40 ring atoms for RY comprises a substituted or unsubstituted phenanthrolyl group derived from the phenanthroline ring represented by formula (1);
- adjacent RY are bonded to each other to form a cyclic structure, or are not bonded to each other
- Z is an oxygen atom, a sulfur atom or a silicon atom;
- when b is 2 to 5, plural Z are the same or different;
- when Z is a silicon atom, R9 and R10 are bonded to the silicon atom, R9 and R10 each independently represent RX as defined in formula (1), and R9 and R10 are optionally bonded to the structure represented by formula (1);
- when Z is a silicon atom, R9 and R10 are not bonded to each other to form a cyclic structure;
- b is an integer of 1 to 5;
- where:
- at least one of X1 to X8 is a carbon atom bonded to L1 or L2 of the formula (1-1);
- X1 to X8 not bonded to L1 or L2 each independently represent CRX or a nitrogen atom;
- each RX is each independently selected from the group consisting of:
- a hydrogen atom,
- a halogen atom,
- a cyano group,
- a nitro group,
- a substituted or unsubstituted hydroxyl group,
- a substituted or unsubstituted carboxyl group,
- a substituted or unsubstituted sulfonyl group,
- a substituted or unsubstituted boryl group,
- a substituted or unsubstituted phosphino group,
- a substituted or unsubstituted mercapto group,
- a substituted or unsubstituted acyl group,
- a substituted or unsubstituted amino group,
- a substituted or unsubstituted silyl group,
- a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
- a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, and
- a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms;
- and
- among X1 to X8, adjacent RX of CRX are bonded to each other to form a cyclic structure, or are not bonded to each other;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b is 1, Z is an oxygen atom, Y4 or Y5 is a carbon atom bonded to L1 or L2, and c is 2, the L1 or L2 closer to the phenanthroline ring represented by formula (1) is a divalent group other than an anthracene group;
- when two of X1 to X8 are carbon atoms bonded to the group represented by formula (2), band c are 1, both of Z are sulfur atoms, Y4 or Y5 is a carbon atom bonded to L1 or and L1 or L2 is a p-phenylene group, L1 or L2 is bonded to any one of X1, X2, X4, X5, X7 and X8,
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), b and c are 1, Z is an oxygen atom or a sulfur atom, Y3 is a carbon atom bonded to L1 or L2, and L1 or L2 is a p-phenylene group, Y4 is CRY, RY being a group other than a phenyl group;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), h and c are 1, Z is an oxygen atom or a sulfur atom, Y6 is a carbon atom bonded to L1 or L2, and L1 or L2 is a p-phenylene group, Y5 is CRY, RY being a group other than a phenyl group;
- when X1 or X8 is a carbon atom bonded to the group represented by formula (2), Z is a silicon atom, Y3 is a carbon atom bonded to L1 or L2, L1 or L2 is a single bond, and Y6 is CRY, RY being the phenanthrolyl group of the heteroaryl group having 5 to 40 ring atoms in CRY for Y6, RY bonds to C at a position other than position 2 of the phenanthrolyl group;
- when X4 or X5 is a carbon atom bonded to the group represented by formula (2), Y2 is a carbon atom bonded to L1 or L2, L1 or L2 is a single bond, and Z is an oxygen atom, Y7 is CRY, RY being a group other than a pyrenyl group;
- and
- when X4 or X5 is a carbon atom bonded to the group represented by formula (2), Y7 is a carbon atom bonded to L1 or L2, L1 or L2 is a single bond, and Z is an oxygen atom;
- Y2 is CRY, RY being a group other a pyrenyl group.
69 more elements
Dependencies are inferred from the claim text.