Organic electroluminescence device
AssigneeUDC Ireland Limited
InventorsHiroo Takizawa, Saki Takada, Eiji Fukuzaki
Life of this patent
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Abstract
The present invention relates to an organic electroluminescence device having high luminous efficiency (for example, external quantum efficiency) and high durability and causing little chromaticity shift after device deterioration. The present invention also relates to an organic electroluminescence device material 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 the light emitting layer contains a metal complex having a group represented by formula (I).
Claims29
An organic electroluminescence device comprising, on a substrate:
- a pair of electrodes;
- and
- at least one organic layer between the electrodes, the organic layer containing a light emitting layer,
- wherein the light emitting layer contains as a light emitting material a metal complex represented by formula (2) having a group represented by the following formula (I), a metal complex represented by formula (14) having the group represented by the following formula (I), or a metal complex represented by formula (A9) having the group represented by the following formula (I):
- wherein R1 represents an alkyl group;
- R2 and R3 each independently represent a hydrogen atom or an alkyl group;
- ns represents an integer of 1 to 6;
- and
- Z represents a saturated 5- to 8-membered ring:
- wherein M21 represents Ir;
- A21 to A23 each independently represent a nitrogen atom or a carbon atom;
- Z21 represents a quinoline ring, an isoquinoline ring, a benzoxazole ring, a pyridine ring, an imidazole ring, or a pyrazole ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, and a cyano group;
- Z22 represents a benzene ring, a pyrazole ring, a pyridine ring, a benzoxazole ring, or a thiophene ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, a methoxy group, an aryl group, and a cyano group;
- L22 and L23 each represent a carbon atom, a nitrogen atom, or an oxygen atom and form together with E21 a bidentate ligand of a phenylpyridine, a pyridylpyridine, a picolinic acid, or an acetylacetone;
- k represents an integer of 1 to 3;
- l represents an integer of 0 to 2;
- k+l is 3;
- S21 and S22 each independently represent the group represented by formula (I);
- n and m each represent an integer of 0 to 4;
- n+m is an integer of 1 to 4;
- and
- S21s or S22s may be the same as or different from every other S21 or S22, respectively:
- wherein A141 to A146 each independently represent a nitrogen atom or a carbon atom;
- Z141 and 2142 each independently represent an isoquinoline ring, a benzoxazole ring, a pyridine ring, an imidazole ring, or a pyrazole ring;
- Z143 and Z144 each independently represent an isoquinoline ring, a benzoxazole ring, a benzene ring, a pyridine ring, an imidazole ring, or a pyrazole ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, a methoxy group, an aryl group, and a cyano group;
- E141 represents a divalent linking group represented by —C(R1)(R2)—, wherein R1 and R2 represent an alkyl group;
- S141 to S144 each independently represent the group represented by formula (I);
- n, m, k and l represents an integer of 0 to 2;
- n+m+k+l is an integer of 1 to 2;
- and
- S141s, S142s, S143S S144s may be the same as or different from every other S141,S142, S143 or S144, respectively:
- wherein Ria to Rli each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a cyano group and at least one of R1a to R1i represents the group represented by formula (I);
- X—Y represents a monoanionic bidentate ligand selected from at least one of a diketone and a picolinic acid derivative;
- and
- n represents an integer of 1 to 3.
A composition comprising a metal complex represented by formula (2) having a group represented by formula (I), a metal complex represented by formula (14) having the group represented by formula (I), or a metal complex represented by formula (A9) having the group represented by formula (I):
- wherein R1 represents an alkyl group;
- R2 and R3 each independently represent a hydrogen atom or an alkyl group;
- ns represents an integer of 1;
- and
- Z represents a saturated 5- to 8-membered ring;
- wherein M21 represents Ir;
- A21 to A23 each independently represent a nitrogen atom or a carbon atom;
- Z21 represents a quinoline ring, an isoquinoline ring, a benzoxazole ring, a pyridine ring, an imidazole ring, or a pyrazole ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, and a cyano group;
- Z22 represents a benzene ring, a pyrazole ring, a pyridine ring, a benzoxazole ring, or a thiophene ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, a methoxy group, an aryl group, and a cyano group;
- L22 and L23 each represent a carbon atom, a nitrogen atom, or an oxygen atom and form together with E21 a bidentate ligand of a phenylpyridine, a pyridylpyridine, a picolinic acid, or an acetylacetone;
- k represents an integer of 1 to 3;
- l represents an integer of 0 to 2;
- k+l is 3;
- S21 and S22 each independently represent the group represented by formula (I);
- n and m each represent an integer of 0 to 4;
- n+m is an integer of 1 to 4;
- and
- S21s or S22s may be the same as or different from every other S21 or S22, respectively:
- wherein A141 to A146 each independently represent a nitrogen atom or a carbon atom;
- Z141 and Z142 each independently represent an isoquinoline ring, a benzoxazole ring, a pyridine ring, an imidazole ring, or a pyrazole ring;
- Z143 and Z144 each independently represent an isoquinoline ring, a benzoxazole ring, a benzene ring, a pyridine ring, an imidazole ring, or a pyrazole ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, a methoxy group, an aryl group, and a cyano group;
- E141 represents a divalent linking group represented by —C(R1)(R2)—, wherein R1 and R2 represent an alkyl group;
- S141 to S144 each independently represent the group represented by formula (I);
- n, m, k and l represents an integer of 0 to 2;
- n+m+k+l is an integer of 1 to 2;
- and
- S141s, S142s, S143s or S144s may be the same as or different from every other S141, S142,S143 or S144, respectively:
- wherein R1a to R1i, each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a cyano group and at least one of R1a to R1irepresents the group represented by formula (I);
- X—Y represents a monoanionic bidentate ligand selected from at least one of a diketone and a picolinic acid derivative;
- and
- n represents an integer of 1 to 3.
A composition comprising a metal complex represented by formula (2) and having a group represented by formula (I):
- wherein M21 represents Ir;
- A21 to A23 each independently represent a nitrogen atom or a carbon atom;
- Z21 represents a quinoline ring, an isoquinoline ring, a benzoxazole ring, a pyridine ring, an imidazole ring, or a pyrazole ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, or a cyano group;
- Z22 represents a benzene ring, a pyrazole ring, a pyridine ring, a benzoxazole ring, or a thiophene ring, and these rings may have a substituent selected from the group consisting of an alkyl group, a fluorine atom, a methoxy group, an aryl group, or a cyano group;
- L22 and L23 each represent a carbon atom, a nitrogen atom, or an oxygen atom and form together with E21 a bidentate ligand of a phenylpyridine, a pyridylpyridine, a picolinic acid, or an acetylacetone;
- k represents an integer of 1 to 3;
- l represents an integer of 0 to 2;
- k+l is 3;
- S21 and S22 each independently represent the group represented by formula (I);
- n and m each represent an integer of 0 to 4;
- n+m is an integer of 1 to 4;
- and wherein
- S21s or S22s may be the same as or different from every other S21 or S22, respectively:
- wherein R1 represents an alkyl group;
- R2 and R3 each independently represent a hydrogen atom or an alkyl group;
- ns represents an integer of 1;
- and
- Z represents a saturated 5- to 8-membered ring.
Dependencies are inferred from the claim text.