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US 11,832,508 B2Granted
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 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 electrode 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).
Claims19
A metal complex represented by formula (2), a metal complex represented by formula (14), or a phosphorescent metal complex containing a monoanionic bidentate ligand represented by the formulae (A1) to (A4) and a metal having an atomic weight of 40 or more, having a group represented by the following formula (I):
- wherein R1 represents an alkyl group;
- each of R2 and R3 independently represents a hydrogen atom or an alkyl group;
- ns represents an integer of 0 to 6;
- and
- Z represents a saturated 5- to 8-membered ring;
- wherein M21 represents a metal belonging to Groups 8 to 11 in the periodic table of elements;
- each of A21 to A23 independently represents a nitrogen atom or a carbon atom;
- Z21 comprises an aromatic nitrogen-containing heterocyclic ring which may be substituted and which may form a condensed ring with other rings;
- Z22 represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may be substituted and which may form a condensed ring with other rings;
- L22 and L23 together with E21 form a bidentate ligand which may be substituted;
- provided that if L22-E21-L23 represents phenylpyridine, then L22-E21-L23 is not further substituted with two alkenyl groups joined to form a ring;
- k represents an integer of 1 to 3;
- l represents an integer of 0 to 2;
- k+l is 2 or 3;
- each of S21 and S22 independently represents a group represented by formula (I);
- each of n and m represents an integer of 0 to 4;
- wherein when n is 1-4, S21 is bonded to a carbon atom of Z21
- n+m is an integer of 1 to 4;
- and
- each S21 or S22 may be the same as or different from every other S21 or S22;
- with the proviso that when Z21 represents an imidazole ring, ns represents an integer of 1 to 6;
- and
- with the proviso that Z21 does not represent pyrazole;
- and Z21 does not represent a pyridine ring having additional rings fused thereto;
- wherein each of A141 to A146 represents a nitrogen atom or a carbon atom;
- Z141 and Z142 each independently represent an aromatic nitrogen-containing heterocyclic ring which may be substituted and which may form a condensed ring with other rings;
- Z143 and Z144 each independently represent an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may be substituted and which may form a condensed ring with other rings;
- E141 represents a divalent linking group;
- S141 to S144 each independently represent the group represented by formula (I);
- n, m, k and l represents an integer of 0 to 4;
- n+m+k+l is an integer of 1 to 4;
- and
- each S141, S142, S143, or S144 may be the same as or different from every other S141, S142, S143 or S144;
- with the proviso that when the metal complex is represented by formula (14), then ns is 1-6;
- wherein each of E1a to E1q independently represents a carbon atom or a heteroatom;
- each of R1a to R1i independently represents a hydrogen atom or a substituent, provided that at least one of R1a to R1i represents a group represented by formula (I);
- two of R1a to R1i may combine with each other to form a saturated or unsaturated, aromatic or non-aromatic ring;
- and
- each of the frameworks represented by formulae (A1) to (A4) has a structure with 18 π-electrons in total;
- with the proviso that when the metal complex is a phosphorescent metal complex containing a monoanionic bidentate ligand represented by the formulae (A1), (A2), (A3), or (A4), then ns is 1-6.
37 more elements
An organic electroluminescence device comprising:
- a pair of electrodes;
- and
- at least one organic layer between the pair of electrodes, the organic layer containing a light emitting layer,
- wherein any one layer of the at least one organic layer contains a metal complex represented by formula (2), a metal complex represented by formula (14), or a phosphorescent metal complex containing a monoanionic bidentate ligand represented by the formulae (A1) to (A4) and a metal having an atomic weight of 40 or more, having a group represented by the following formula (I):
- wherein R1 represents an alkyl group;
- each of R2 and R3 independently represents a hydrogen atom or an alkyl group;
- ns represents an integer of 0 to 6;
- and
- Z represents a saturated 5- to 8-membered ring;
- wherein M21 represents a metal belonging to Groups 8 to 11 in the periodic table of elements;
- each of A21 to A23 independently represents a nitrogen atom or a carbon atom;
- Z21 comprises an aromatic nitrogen-containing heterocyclic ring which may be substituted and which may form a condensed ring with other rings;
- Z22 represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may be substituted and which may form a condensed ring with other rings;
- L22 and L23 together with E21 form a bidentate ligand which may be substituted;
- provided that if L22-E21-L23 represents phenylpyridine, then L22-E21-L23 is not further substituted with two alkenyl groups joined to form a ring;
- k represents an integer of 1 to 3;
- l represents an integer of 0 to 2;
- k+l is 2 or 3;
- each of S21 and S22 independently represents a group represented by formula (I);
- each of n and m represents an integer of 0 to 4;
- wherein when n is 1-4, S21 is bonded to a carbon atom of Z21
- n+m is an integer of 1 to 4;
- and
- each S21 or S22 may be the same as or different from every other S21 or S22;
- with the proviso that when Z21 represents an imidazole ring, ns represents an integer of 1 to 6;
- and
- with the proviso that Z21 does not represent pyrazole;
- and Z21 does not represent a pyridine ring having additional rings fused thereto;
- wherein each of A141 to A146 represents a nitrogen atom or a carbon atom;
- Z141 and Z142 each independently represent an aromatic nitrogen-containing heterocyclic ring which may be substituted and which may form a condensed ring with other rings;
- Z143 and Z144 each independently represent an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may be substituted and which may form a condensed ring with other rings;
- E141 represents a divalent linking group;
- S141 to S144 each independently represent the group represented by formula (I);
- n, m, k and l represents an integer of 0 to 4;
- n+m+k+l is an integer of 1 to 4;
- and
- each S141, S142, S143, or S144 may be the same as or different from every other S141, S142, S143 or S144;
- with the proviso that when the metal complex is represented by formula (14), then ns is 1-6;
- wherein each of E1a to E1q independently represents a carbon atom or a heteroatom;
- each of R1a to R1i independently represents a hydrogen atom or a substituent, provided that at least one of R1a to R1i represents a group represented by formula (I);
- two of R1a to R1i may combine with each other to form a saturated or unsaturated, aromatic or non-aromatic ring;
- and
- each of the frameworks represented by formulae (A1) to (A4) has a structure with 18 π-electrons in total;
- with the proviso that when the metal complex is a phosphorescent metal complex containing a monoanionic bidentate ligand represented by the formulae (A1), (A2), (A3), or (A4), then ns is 1-6.
41 more elements
Dependencies are inferred from the claim text.