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US 6,875,523 B2Granted
Photoactive lanthanide complexes with phosphine oxides, phosphine oxide-sulfides, pyridine N-oxides, and phosphine oxide-pyridine N-oxides, and devices made with such complexes
AssigneeE. I. Du Pont de Nemours and Company
InventorsVladimir Grushin, Norman Herron, Viacheslav Alexandrovich Petrov, Nora Sabina Radu, Ying Wang
Life of this patent
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Abstract
The present invention is generally directed to luminescent lanthanide compounds with phosphine oxide, phosphine oxide-sulfide, pyridine N-oxide, and phosphine oxide-pyridine N-oxide ligands. It also relates to electronic devices in which the active layer includes a lanthanide complex.
Claims12
A lanthanide compound having one of Formulae IX-A and IX-B below:
- Ln(β-enolate)3(monophosphine oxide)1 (IX-A)
- Ln(β-enolate)3(monophosphine oxide)2 (IX-B)
- where:
- in Formulae (IX-A) and (IX-B):
- monophosphine oxide has Formula I:
- O2P(O)—Z (I)
- such that:
- 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, and
- 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.
8 more elements
A lanthanide compound having one of Formulae IX-A and IX-B below:
- Ln(β-enolate)3(monophosphine oxide)1 (IX-A)
- Ln(β-enolate)3(monophosphine oxide)2 (IX-B)
- and selected from Compound 1-a to Compound 1-b below:
- TABLE 1
- Compound
- Ln
- β-enolate
- phosphine oxide
- 1 or 2
- 1-a
- Eu
- acac
- dppmO
- 2
- 1-b
- Eu
- acac
- dppeO
- 2
- 1-c
- Eu
- acac
- dpppO
- 2
- 1-d
- Eu
- acac
- dppbO
- 2
- 1-e
- Eu
- acac
- F5tpO
- 2
- 1-f
- Eu
- DI
- dppmO
- 2
- 1-g
- Eu
- DI
- dppeO
- 2
- 1-h
- Eu
- DI
- dpppO
- 2
- 1-i
- Eu
- DI
- dppbO
- 2
- 1-j
- Eu
- DI
- F5tpO
- 2
- 1-k
- Eu
- TMH
- dppmO
- 1
- 1-l
- Eu
- TMH
- dppeO
- 1
- 1-m
- Eu
- TMH
- dpppO
- 1
- 1-n
- Eu
- TMH
- dppbO
- 1
- 1-o
- Eu
- TMH
- F5tpO
- 1
- 1-p
- Eu
- TTFA
- dppmO
- 2
- 1-q
- Eu
- TTFA
- dppeO
- 2
- 1-r
- Eu
- TTFA
- dpppO
- 2
- 1-s
- Eu
- TTFA
- dppbO
- 2
- 1-t
- Eu
- TTFA
- F5tpO
- 2
- 1-u
- Eu
- FOD
- dppmO
- 2
- 1-v
- Eu
- FOD
- dppeO
- 2
- 1-w
- Eu
- FOD
- dpppO
- 2
- 1-x
- Eu
- FOD
- dppbO
- 2
- 1-y
- Eu
- FOD
- F5tpO
- 2
- 1-z
- Eu
- F7acac
- dppmO
- 2
- 1-aa
- Eu
- F7acac
- dppeO
- 2
- 1-ab
- Eu
- F7acac
- dpppO
- 2
- 1-ac
- Eu
- F7acac
- dppbO
- 2
- 1-ad
- Eu
- F7acac
- F5tpO
- 2
- 1-ae
- Tb
- acac
- dppmO
- 2
- 1-af
- Tb
- acac
- dppeO
- 2
- 1-ag
- Tb
- acac
- dpppO
- 2
- 1-ah
- Tb
- acac
- dppbO
- 2
- 1-ai
- Tb
- acac
- F5tpO
- 2
- 1-aj
- Tb
- TMH
- dppmO
- 1
- 1-ak
- Tb
- TMH
- dppeO
- 1
- 1-al
- Tb
- TMH
- dpppO
- 1
- 1-am
- Tb
- TMH
- dppbO
- 1
- 1-an
- Tb
- TMH
- F5tpO
- 1
- 1-ao
- Tb
- TTFA
- dppmO
- 2
- 1-ap
- Tb
- TTFA
- dppeO
- 2
- 1-aq
- Tb
- TTFA
- dpppO
- 2
- 1-ar
- Tb
- TTFA
- dppbO
- 2
- 1-as
- Tb
- TTFA
- F5tpO
- 2
- 1-at
- Tb
- F7acac
- dppmO
- 2
- 1-au
- Tb
- F7acac
- dppeO
- 2
- 1-av
- Tb
- F7acac
- dpppO
- 2
- 1-aw
- Tb
- F7acac
- dppbO
- 2
- 1-ax
- Tb
- F7acac
- F5tpO
- 2
- 1-ay
- Tm
- TMH
- dppmO
- 1
- 1-az
- Tm
- TMH
- dppeO
- 1
- 1-ba
- Tm
- TMH
- dpppO
- 1
- 1-bb
- Tm
- TMH
- dppbO
- 1
- 1-bc
- Tb
- PMBP
- F5tpO
- 2
- 1-bd
- Eu
- F6acac
- dppmO
- 2
- 1-be
- Eu
- F6acac
- dppeO
- 2
- wherein:
- acac is 2,4-pentanedionate,
- DI is 1,3-diphenyl-1,3-propanedionate,
- TMH is 2,2,6,6-tetramethyl-3,5-heptanedionate,
- TTFA is 1-(2-thienyl)4,4,4-trifluoroacetonate,
- FOD is 7,7-dimethyl-1,1,1,2,2,3,3-heptafluoro-4,6-octanedionate,
- F6acac is 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate,
- F7acac is 1,1,1,3,5,5,5-heptafluoro-2,4-pentanedionate,
- PMBP is 1-phenyl -3-methyl-4-i-butyryl -5-pyrazolinonate,
- dppmO is (diphenylphosphinomethyl)diphenylphosphine oxide,
- dppeO is (2-diphenylphosphinoethyl)diphenylphosphine oxide,
- dpppO is (3-diphenylphosphinoethyl)diphenylphosphine oxide,
- dppbO is (4-diphenylphosphinoethyl)diphenylphosphine oxide, and
- F5tpO is tris(pentafluorophenyl)phosphine oxide.
305 more elements
Dependencies are inferred from the claim text.