US Patent No. 9,554,442

ORGANIC METAL COMPLEX, AND ORGANIC LIGHT EMITTING DEVICE AND DISPLAY APPARATUS USING THE SAME


Patent No. 9,554,442
Issue Date January 24,2017
Title Organic Metal Complex, And Organic Light Emitting Device And Display Apparatus Using The Same
Inventorship Jun Kamatani, Tokyo (JP)
Masashi Hashimoto, Tokyo (JP)
Satoshi Igawa, Fujisawa (JP)
Shinjiro Okada, Kamakura (JP)
Assignee Canon Kabushiki Kaisha, Tokyo (JP)

Claim of US Patent No. 9,554,442

1. An organic light emitting device comprising:
an anode;
a cathode; and
an emission layer formed of an organic compound, which is sandwiched between the anode and the cathode,
wherein the emission layer formed of an organic compound comprises an organic metal complex having a structure represented
by the following general formula (1):

MLmL?n  (1)

wherein L and L?, which are different from each other, each represent a bidentate ligand;
wherein m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n is 3;
wherein M represents Ir;
wherein the partial structure MLm has a structure represented by the following general formula (8)


wherein the benzene ring with R41-R44 attached thereto in the formula (8) is further represented by any one of the following formulae:


wherein *1 shows the connection to the Ir;
wherein *2 shows the connection to the benzo[f]isoquinoline ring represented in the formula (8), and
wherein R88 to R102, which may be identical to or different from each other, each represent a hydrogen atom, a halogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted
or unsubstituted aralkyl group, an amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted
heterocyclic group;

wherein the partial structure ML?n has a structure represented by any one of the following general formulae (10) to (12)


wherein R45 to R52, which may be identical to or different from each other, each represent a hydrogen atom, a halogen atom, a substituted or
unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted
or unsubstituted aralkyl group, an amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted
heterocyclic group, and R47 and R48 may be bonded to form a benzene ring that is fused with the benzo[f]isoquinoline ring represented in the formula (8); and

wherein R65 to R79, which may be identical to or different from each other, each represent a hydrogen atom, a halogen atom, a substituted or
unsubstituted alkyl group, an alkoxy group, an aralkyl group, a substituted amino group, a substituted or unsubstituted aryl
group, or a substituted or unsubstituted heterocyclic group, and adjacent substituents among R65 to R68, may be bonded to form a ring that is fused with the benzene ring represented in the formula (10) and adjacent substituents
among R77 to R79 may be bonded to form a ring that is fused with the backbone represented in the formula (12).