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US 2012/0100628 A1Published application
Emissive and broadband nonlinear absorbing metal complexes and ligands as oled, optical switching or optical sensing materials
AssigneeNDSU Research Foundation
InventorsWenfang Sun, Bingguang Zhang, Rui Liu, Pin Shao, Zhiqiang Ji, Zhongjing Li
Life of this patent
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Abstract
Platinum (II) terdentate or bidentate complexes with non-linear optical properties are provided. The complexes have a broadband spectral and temporal response, and strong reverse saturable absorption and two-photon absorption in the visible and the near-IR region. As such, the complexes are useful for organic light-emitting diodes and optical-switching or sensing devices.
Claims29
A ligand of formula (I):
- wherein:
- R10 is H or —ORa;
- R2 and R3 are each independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —(O—CH2—CH2)n—OCH3;
- R4 is H, halo, aryl, heterocyclyl, arylalkynyl, heterocyclylalkyl, arylalkynyl, arylalkenyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —CH═N—NH—Rf;
- X is C or N;
- each n is independently an integer from 1-12;
- each Ra, Rb, Rc, Rd, Re, and Rf is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl or C2-C24 alkynyl, aryl, heterocyclyl, arylalkyl, and heterocyclylalkyl;
- and
- Y is a bond, —CH═CH—, —CH═CH-Ph-, or —C≡C—;
- wherein when the ligand of formula (I) bears a charge, it further comprises one or more counterions.
7 more elements
A ligand of formula (II):
- wherein:
- the dashed line represents the presence or absence of an optionally substituted aromatic ring or fused aromatic rings;
- R2 and R3 are each independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —(O—CH2—CH2)m—OCH3;
- R4 is H, halo, aryl, heterocyclyl, arylalkynyl, arylalkyl, arylalkenyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, or —CH═N—NH—Rf;
- each R15 is independently selected from H, halo, aryl, heterocyclyl, arylalkynyl, C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl;
- each m is independently an integer from 1-12;
- and
- each Rb, Rc, Rd, Re, and Rf is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, heterocyclyl, arylalkyl, heterocyclylalkyl and aryl,
- wherein when the ligand of formula (II) bears a charge, it further comprises one or more counterions.
6 more elements
A ligand of formula (III):
- wherein:
- each R1 is independently a group of the following formula:
- each n equals to 0 or 1;
- each R2 and R3 is independently C1-C24 alkyl, C2-C24 alkenyl or C2-C24 alkynyl, or —(O—CH2—CH2)m—OCH3;
- each R4 is independently H, halo, aryl, arylalkynyl, heterocyclyl, arylalkyl, arylalkenyl, heterocyclylalkyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —CH═N—NH—Rf;
- and
- each Rb, Rc, Rd, Re, and Rf is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, heterocyclyl, arylalkyl, heterocyclylalkyl and aryl;
- each m is independently an integer from 1-12;
- and
- wherein the dashed line represents the presence or absence of an optionally substituted aromatic ring or fused aromatic rings;
- and
- wherein when the ligand of formula (III) bears a charge, it further comprises one or more counterions.
9 more elements
A metal complex of formula (IV):
- wherein:
- R10 is H or —ORa;
- R2 and R3 are each independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —(O—CH2—CH2)m—OCH3;
- R4 is H, halo, aryl, heterocyclyl, arylalkyl, heterocyclylalkyl, arylalkynyl, arylalkenyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —CH═N—NH—Rf;
- A is selected from halo,
- and —C≡C—Rg;
- X═C or N;
- each m is independently an integer from 1-12;
- each Ra, Rb, Rc, Rd, Re, Rf, and Rg is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl or C2-C24 alkynyl, aryl, heterocyclyl, arylalkyl, arylalkynyl and heterocyclylalkyl;
- and
- Y is a bond, —CH═CH—, —CH═CH-Ph-, or —C≡C—;
- M is a metal ion;
- and
- wherein when the complex of formula (IV) bears a charge, it further comprises one or more counterions.
11 more elements
A metal complex of formula (V):
- wherein:
- the dashed line represents the presence or absence of an optionally substituted aromatic ring or fused aromatic rings;
- R2 and R3 are each independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —(O—CH2—CH2)m—OCH3;
- R4 is H, halo, aryl, heterocyclyl, arylalkynyl, arylalkyl, arylalkenyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, or —CH═N—NH—Rf;
- R15 is each independently selected from H, halo, aryl, heterocyclyl, arylalkynyl, C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl;
- A is selected from halo and —C≡C—Rg;
- M is a metal ion;
- each m is independently an integer from 1-12;
- and
- each Rb, Rc, Rd, Re, Rf, and Rg is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, heterocyclyl, arylalkyl, heterocyclylalkyl, arylalkynyl and aryl,
- wherein when the complex of formula (V) bears a charge, it further comprises one or more counterions.
8 more elements
A metal complex of formula (VI):
- wherein:
- the dashed line represents the presence or absence of an optionally substituted aromatic ring or fused aromatic rings;
- each R1 is independently a group of the following formula:
- each n equals to 0 or 1 each R2 and R3 is independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, or —(O—CH2—CH2)m—OCH3;
- each m is independently an integer from 1-12;
- each R4 is independently H, halo, aryl, arylalkynyl, heterocyclyl, arylalkyl, arylalkenyl, heterocyclylalkyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —CH═N—NH—Rf;
- and
- each Rb, Rc, Rd, Re, and Rf is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, heterocyclyl, arylalkyl, heterocyclylalkyl and aryl;
- A is selected from halo and —C≡C—Rg;
- each Rg is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, heterocyclyl, arylalkyl, heterocyclylalkyl, arylalkynyl and aryl;
- and
- M is a metal ion;
- wherein when the complex of formula (VI) bears a charge, it further comprises one or more counterions.
10 more elements
A metal complex of formula (VII):
- wherein
- M is a metal ion;
- the dashed line represents the presence or absence of an optionally substituted aromatic ring or fused aromatic rings;
- each R1 is independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, arylalkynyl or —(O—CH2—CH2)m—OCH3;
- each R2 and R3 is independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, or —(O—CH2—CH2)n—OCH3;
- each R4 is independently H, halo, aryl, arylalkynyl, heterocyclyl, arylalkyl, arylalkenyl, heterocyclylalkyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl or —CH═N—NH—Rf;
- each m is independently an integer from 1-12;
- each Rb, Rc, Rd, Re, and Rf is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, arylalkyl, heterocyclylalkyl and aryl;
- and
- wherein when the complex of formula (VII) bears a charge, it further comprises one or more counterions.
7 more elements
A metal complex of formula (VIII):
- wherein
- M is a metal ion;
- the dashed line represents the presence or absence of an optionally substituted aromatic ring or fused aromatic rings;
- each R1 is independently C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, arylalkynyl or —(O—CH2—CH2)m—OCH3;
- each R11 is independently H, halo, aryl, arylalkynyl, heterocyclyl, arylalkyl, arylalkenyl, heterocyclylalkyl, —C(O)Rb, —NRcRd, —ORe, —NO2, —CHO, C1-C24 alkyl, C2-C24 alkenyl, and C2-C24 alkynyl;
- each m is independently an integer from 1-12;
- each Rb, Rc, Rd, and Re is independently selected from H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, arylalkyl, heterocyclylalkyl and aryl;
- and
- wherein when the complex of formula (VIII) bears a charge, it further comprises one or more counterions.
6 more elements
Dependencies are inferred from the claim text.