Photoactive lanthanide complexes with phosphine oxides, phosphine oxide-sulfides, pyridine N-oxides, and phosphine oxide-pyridine N-oxides, and devices made with such complexes

A lanthanide compound comprising having one of Formulae IX through XV below:

• Ln(β-enolate)3(monophosphine oxide)1 (IX-A) Ln(β-enolate)3(monophosphine oxide)2 (IX-B) [Ln(β-enolate)3]1(bisphosphine dioxide)1 (X-A) [Ln(β-enolate)3]2(bisphosphine dioxide)1 (X-B) [Ln(β-enolate)3]1(trisphosphine trioxide)1 (XI-A) [Ln(β-enolate)3]2(trisphosphine trioxide)1 (XI-B) [Ln(β-enolate)3]3(trisphosphine trioxide)1 (XI-C) Ln(β-enolate)3(bisphosphine oxide-sulfide)1 (XII-A) Ln(β-enolate)3(bisphosphine oxide-sulfide)2 (XII-B) Ln2(β-enolate)6(pyridine-N-oxide)3 (XIII) Ln(β-enolate)3(phosphine oxide-pyridine N-oxide)1 (XIV) Ln2(β-enolate)6(bisphosphine monoxide)2MX2 (XV)
• where:
• in Formulae (IX-A) and (IX-B):
• monophosphine oxide has Formula I shown in FIG. 1;
• in Formulae (X-A) and (X-B):
• bisphosphine dioxide has Formula II, shown in FIG. 1;
• where in Formula , x is 2, y is 1 and r is 1;
• in Formulae (XI-A), (XI-B), and(XI-C):
• trisphosphine trioxide has Formula II, shown in FIG. 1;
• where in Formula II, x is 1, y is 2, and r is 1;
• in Formulae (XII-A) and (XII-B):
• bis-phosphine oxide-sulfide has Formula III, shown in FIG. 1;
• in Formula (XIII):
• pyridine N-oxide has Formula IV, Formula V or Formula VI, shown in FIG. 2;
• in Formula (XIV):
• phosphine oxide-pyridine N-oxide has Formula VII, shown in FIG. 3;
• in Formula XV:
• bisphosphine monoxide has Formula II, shown in FIG. 1;
• where in Formula II, x is 2, y is 1, and r is 0;
• M is a transition metal;
• X is a monoanionic ligand;
• such that:
• in each of Formulae I, II and III:
• Q is the same or different at each occurrence and is selected from C6HnF5-n, and Cm(H+F)2m+1,
• m is an integer from 1 to 12, and
• n is 0 or an integer from 1 to 5,
• in Formula I:
• Z is selected from Q and pyridiyl, with the provision that when Z is Q, there is at least one F substituent on at least one Q group,
• in each of Formulae II and III:
• LG is the same or different at each occurrence and is a linking group selected from Cm(H+F)2m, arylene, cyclic heteroalkylene, heteroarylene, alkyleneheteroarylene, ferrocenediyl, and o-carboranediyl,
• in FormulaII:
• r is the same or different at each occurrence and is 0 or 1,
• x is 1 or 2, and
• y is 1 or 2, with the provision that x+y=3,
• in each of Formulae IV through VII:
• Y is the same or different at each occurrence and is selected from —CN, —OR1, —OH, —C(O)O R1, —Rf, aryl, X, —NO2, and —SO2 R1,
• R1 is CsH2s+1,
• Rf is CsF2s+1
• X is F, Cl, Br, or I,
• s is an integer from 1 to 6,
• in Formula IV:
• α is 0 or an integer from 1 to 5,
• in Formulae V through VII:
• βis 0 or an integer from 1 to 4,
• in Formula V:
• δ is 0 or an integer from 1 to 3, and
• in Formula VII:
• m is 0 or an integer from 1-12.