Dinuclear platinum (II) red emitters for OLED applications
View Patent ↗Platinum (II) complexes (“Pt(II) complexes”) that can emit in the red and/or deep red regions and methods of making and using thereof are described. These Pt(II) complexes can have dinuclearity with close Pt—Pt contact and close interplanar distance, allowing for high emission quantum yield, such as >50%, short emission lifetime, such as <3 μs, and high radiative decay rate, such as in the order of 10 5 s −1 . The Pt(II) complexes disclosed herein can be included in organic light-emitting devices, such as organic light-emitting diodes (“OLEDs”), for use in commercial applications. OLEDs containing these red-emitting Pt(II) complexes can have current efficiency and/or external quantum efficiency that are comparable or higher than commercially available red emitters and prolonged operational lifetime, such as a LT95 at 1000 nits>9000 h for a red OLED.
1 . A platinum (II) complex having a structure:
wherein:
(a) R 5 , R 6 , R 7 , and R 8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, alkoxy, or aroxy;
(b) R 9 and R 10 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol;
(c) when present R 11 -R 14 , R 21 -R 24 and R 27 -R 34 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally R 11 and R 12 together, R 12 and R 13 together, R 13 and R 14 together, R 21 and R 22 together, R 22 and R 23 together, R 23 and R 24 together, R 27 and R 28 together, R 28 and R 29 together, R 29 and R 30 together, R 31 and R 32 together, R 32 and R 33 together, and/or R 33 and R 34 together form a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted cycloalkynyl, or a substituted or unsubstituted heterocyclyl;
(d) each is independently absent, a bond, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted heterocyclyl, an alkoxy, an aroxy, an ether, a polyether, a sulfonyl, or a thioether;
(e) X 1 ′-X 4 ′ and Y 1 ′-Y 8 ′ are independently O, S, CR 15 , or NR 18 , R 15 and R 18 are independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol;
(f) the substituents are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, a halogen, a hydroxyl, a phenoxy, an aroxy, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, a phosphonyl, or a thiol, or a combination thereof, and
(g) wherein at least one of Y 1 ′-Y 4 ′ is NR 18 .
2 . The platinum (II) complex of claim 1 having a structure:
wherein:
(a) R 5 , R 6 , R 7 , and R 8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, alkoxy, or aroxy;
(b) R 9 and R 10 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol;
(c) R 11 -R 14 and R 21 -R 24 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally R 11 and R 12 together, R 12 and R 13 together, R 13 and R 14 together, R 21 and R 22 together, R 22 and R 23 together, R 23 and R 24 together form a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted cycloalkynyl, or a substituted or unsubstituted heterocyclyl;
(d) each is independently absent, a bond, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted heterocyclyl, an alkoxy, an aroxy, an ether, a polyether, a sulfonyl, or a thioether;
(e) X 1 ′, X 2 ′, Y 1 ′-Y 8 ′ are independently O, S, CR 15 , or NR 18 , R 15 and R 18 can are independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol; and
(f) the substituents are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, a halogen, a hydroxyl, a phenoxy, an aroxy, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, a phosphonyl, or a thiol, or a combination thereof.
3 . The platinum (II) complex of claim 1 having a structure:
wherein:
(a) R 5 , R 6 , R 7 , and R 8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, alkoxy, or aroxy;
(b) R 9 and R 10 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol;
(c) R 11 -R 14 , R 16 , R 17 , and R 19 -R 24 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally R 11 and R 12 together, R 12 and R 13 together, R 13 and R 14 together, R 16 and R 17 together, R 19 and R 20 together, R 21 and R 22 together, R 22 and R 23 together, and/or R 23 and R 24 together form a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted cycloalkynyl, or a substituted or unsubstituted heterocyclyl;
(d) is absent, a single bond, a double bond, a triple bond, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted heterocyclyl, an alkoxy, an aroxy, an ether, a polyether, a sulfonyl, or a thioether;
(e) X 1 ′, X 2 ′, Y′, Y 2 ′, Y 3 ′, and Y 4 ′ are independently O, S, CR 15 , or NR 18 , R 15 and R 18 are independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol; and
(f) the substituents are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, a halogen, a hydroxyl, a phenoxy, an aroxy, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, a phosphonyl, or a thiol, or a combination thereof.
4 . The platinum (II) complex of claim 1 having a structure:
wherein:
(a) R 5 , R 6 , R 7 , and R 8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, alkoxy, or aroxy;
(b) R 9 and R 10 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol;
(c) R 11 -R 14 , R 21 -R 24 , and R 27 -R 34 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, oxo, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally R 11 and R 12 together, R 12 and R 13 together, R 13 and R 14 together, R 21 and R 22 together, R 22 and R 23 together, R 23 and R 24 , R 27 and R 28 together, R 28 and R 29 together, R 29 and R 30 together, R 31 and R 32 together, R 32 and R 33 together, and/or R 33 and R 34 together, form a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted cycloalkynyl, or a substituted or unsubstituted heterocyclyl;
(d) is absent, a single bond, a double bond, a triple bond, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted heterocyclyl, an alkoxy, an aroxy, an ether, a polyether, a sulfonyl, or a thioether;
(e) X 3 ′ and X 4 ′ are independently CR 25 or NR 26 , R 25 and R 26 are independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol; and
(f) the substituents are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, a halogen, a hydroxyl, a phenoxy, an aroxy, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, a phosphonyl, or a thiol, or a combination thereof.
5 . The platinum (II) complex of claim 4 , wherein X 3 ′ and X 4 ′ are independently CR 25 or NR 26 , R 25 and R 26 are independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
6 . The platinum (II) complex of claim 4 , wherein R 27 -R 34 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, or hydroxyl.
7 . The platinum (II) complex of claim 1 wherein R 9 and R 10 are independently hydrogen or substituted or unsubstituted alkyl.
8 . The platinum (II) complex of claim 1 , wherein R 11 , R 12 , R 21 , R 22 are hydrogen or R 11 and R 12 together forms and/or R 21 and R 22 together forms
wherein:
(a) Z′ is O, S, CR 39 , or NR 40 , R 39 and R 40 are independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol;
(b) J 1 ′ and J 2 ′ are independently
R 41 and R 42 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally J 1 ′ and J 2 ′ together form a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, or a substituted or unsubstituted cycloalkynyl;
(c) n7 is an integer from 0 to 4; and
(d) R 35 -R 38 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, halogen, hydroxyl, amino, azido, alkoxy, aroxy, cyano, isocyano, carbonyl, nitro, or thiol.
9 . The platinum (II) complex of claim 8 , wherein n7 and n8 are 0 and Z′ is O, S, or NR 40 , each occurrence of R 40 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, or hydroxyl.
10 . The platinum (II) complex of claim 8 , wherein R 35 -R 38 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, or aroxy.
11 . The platinum (II) complex of claim 1 , wherein the between R 5 and R 8 , between R 6 and R 7 , between R 5 and R 7 , and/or between R 6 and R 8 is absent or wherein
have a structure:
wherein:
(a) A′ and B′ are independently substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclyl; and
(b) each occurrence of L 5 is independently ether, polyether, alkoxyl, sulfonyl, thioether, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl.
12 . The platinum (II) complex of claim 11 , wherein A′ and B′ are independently substituted or unsubstituted aryl or substituted or unsubstituted polyaryl; and L 5 has a structure:
wherein:
(a) Q 1 ′ and Q 2 ′ are independently absent, O or S; and
(b) n9 is an integer from 1 to 10.
13 . A platinum (II) complex having any one of the following structures:
14 . The platinum (II) complex of claim 1 having:
an emission lifetime (τ em ) of up to 3.0 μs, up to 2.5 μs, up to 2.0 μs, in a range from 0.5 μs to 3.0 μs, from 0.8 μs to 3.0 μs, from 1.0 μs to 3.0 μs, from 0.5 μs to 2.5 μs, from 0.8 μs to 2.5 μs, from 1.0 μs to 2.5 μs, from 0.5 μs to 2.0 μs, from 0.8 μs to 2.0 μs, or from 1.0 μs to 2.0 μs, in solution or in films; or
a radiative decay rate (k r ) of at least 1.0×10 5 s −1 , at least 1.4×10 5 s −1 , in a range from 1.0×10 5 s −1 to 25.0×10 5 s −1 , from 1.0×10 5 s −1 to 20.0×10 5 s −1 , from 1.0×10 5 s −1 to 15.0×10 5 s −1 , from 1.0×10 5 s −1 to 12.0×10 5 s −1 , from 1.0×10 5 s −1 to 10.0×10 5 s −1 , from 1.0×10 5 s −1 to 8.0×10 5 s −1 , from 1.0×10 5 s −1 to 6.0×10 5 s −1 , from 1.4×10 5 s −1 to 25.0×10 5 s −1 , from 1.4×10 5 s −1 to 20.0×10 5 s −1 , from 1.4×10 5 s −1 to 15.0×10 5 s −1 , from 1.4×10 5 s −1 to 12.0×10 5 s −1 , from 1.4×10 5 s −1 to 10.0×10 5 s −1 , from 1.4×10 5 s −1 to 8.0×10 5 s −1 , or from 1.4×10 5 s −1 to 6.0×10 5 s −1 , in solution or in films; or
an emission quantum yield (“QY”) of at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, in a range from 50% to 90%, from 55% to 90%, from 60% to 90%, from 50% to 80%, from 55% to 80%, or from 60% to 80%, in solution or in films, at room temperature; or
a maximum emission wavelength (“λ max ”) in a range from 600 nm to 760 nm, from 604 nm to 733 nm, from 600 nm to 700 nm, or from 700 nm to 1000 nm; or
a full width at half maximum (“FWHM”) of up to 270 nm, up to 250 nm, up to 200 nm, up to 180 nm, up to 160 nm, up to 145 nm, up to 135 nm, up to 120 nm, up to 110 nm, up to 100 nm, up to 90 nm, up to 80 nm, in a range from 50 nm to 270 nm, from 50 nm to 250 nm, from 50 nm to 200 nm, from 50 nm to 180 nm, from 50 nm to 160 nm, from 50 nm to 145 nm, from 50 nm to 110 nm, from 60 nm to 145 nm, from 60 nm to 110 nm, from 70 nm to 145 nm, or from 70 nm to 110 nm; or
a combination thereof.
15 . An organic light-emitting component comprising one or more light emitting layers, wherein the one or more light emitting layers comprise one or more platinum (II) complexes of claim 1 , optionally wherein the organic light-emitting component is an organic light-emitting diode (“OLED”) or a light-emitting electrochemical cell (“LEEC”).
16 . The organic light-emitting component of claim 15 , wherein the one or more light emitting layers further comprise one or more host materials, and wherein the total concentration of the one or more host materials is greater than the total concentration of the one or more complexes in the one or more light emitting layers.
17 . The organic light-emitting component of claim 16 , wherein the total concentration of the one or more platinum (II) complexes in the one or more light emitting layers is up to 50 wt %, up to 40 wt %, up to 30 wt %, up to 20 wt %, at least 1 wt %, in a range from about 1 wt % to about 50 wt %, from about 1 wt % to about 40 wt %, from about 1 wt % to about 30 wt %, from about 1 wt % to about 20 wt %, from about 2 wt % to about 50 wt %, from about 2 wt % to about 40 wt %, from about 2 wt % to about 30 wt %, from about 2 wt % to about 20 wt %, from about 4 wt % to about 50 wt %, from about 4 wt % to about 40 wt %, from about 4 wt % to about 30 wt %, from about 4 wt % to about 20 wt %, from about 1 wt % to about 16 wt %, from about 2 wt % to about 16 wt %, from about 4 wt % to about 16 wt %.
18 . The organic light-emitting component of claim 15 further comprising an anode, a cathode, a hole transport region, and an electron transport region,
wherein the hole transport region comprises a hole injection layer and/or a hole transport layer, and optionally an electron blocking layer,
wherein the electron transport region comprises an electron transport layer and/or an electron injection layer, and optionally a hole blocking layer,
wherein the light emitting layer is located in between the anode and the cathode,
wherein the hole transport region is located in between the anode and the light-emitting layer, and
wherein the electron transport region is located in between the cathode and the light emitting layer.
19 . The organic light-emitting component of claim 15 having a current efficiency (“CE”) at 1000 cd/m 2 of at least 18 cd/A, at least 20 cd/A, at least 25 cd/A, at least 30 cd/A, in a range from 18 cd/A to 60 cd/A, from 20 cd/A to 60 cd/A, from 25 cd/A to 60 cd/A, from 30 cd/A to 60 cd/A, from 18 cd/A to 50 cd/A, from 20 cd/A to 50 cd/A, from 25 cd/A to 50 cd/A, from 30 cd/A to 50 cd/A, from 18 cd/A to 40 cd/A, from 20 cd/A to 40 cd/A, from 25 cd/A to 40 cd/A, or from 30 cd/A to 40 cd/A; or
a power efficiency (“PE”) at 1000 cd/m 2 of at least 6 lm/W, at least 10 lm/W, at least 15 lm/W, at least 20 lm/W, at least 25 lm/W, in a range from 6 lm/W to 60 lm/W, from 10 lm/W to 60 lm/W, from 15 lm/W to 60 lm/W, from 20 lm/W to 60 lm/W, from 6 lm/W to 50 lm/W, from 10 lm/W to 50 lm/W, from 15 lm/W to 50 lm/W, from 20 lm/W to 50 lm/W, from 6 lm/W to 40 lm/W, from 10 lm/W to 40 lm/W, from 15 lm/W to 40 lm/W, from 20 lm/W to 40 lm/W, from 6 lm/W to 35 lm/W, from 10 lm/W to 35 lm/W, from 15 lm/W to 35 lm/W, from 20 lm/W to 35 lm/W, from 6 lm/W to 30 lm/W, from 10 lm/W to 30 lm/W, from 15 lm/W to 30 lm/W, or from 20 lm/W to 30 lm/W; or
an external quantum efficiency (“EQE”) at 1000 cd m −2 of at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, in a range from 10% to 40%, from 10% to 20%, from 10% to 20%, from 11% to 40%, from 11% to 30%, from 11% to 20%, from 12% to 20%, from 12% to 40%, from 12% to 30%, from 13% to 20%, from 13% to 40%, from 13% to 30%, from 14% to 20%, from 14% to 40%, from 14% to 30%, from 15% to 40%, from 15% to 30%, or from 15% to 20% for a single layer of the platinum (II) complexes; or
a LT95 at 1000 cd/m 2 of at least 9000 h, at least 9300 h, or at least 9500 h, or wherein the one or more platinum (II) complexes have a λ max in a range from 700 nm to 1000 nm and the organic light-emitting component has a LT95 at 1000 cd/m 2 of at least 1000 h, at least 1500 h, or at least 2000 h; or
a combination thereof.
20 . A device comprising one or more organic light-emitting components of claim 15 , wherein the device is a stationary visual display unit, a mobile visual display unit, an illumination device, a wearable device, or a medical monitoring device.
21 . The platinum (II) complex of claim 1 , wherein at least one of Formula III′, at least one of Formula IV, the of Formula III″, and the of Formula IV′ are independently a bond, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted heterocyclyl, an alkoxy, an aroxy, an ether, a polyether, a sulfonyl, or a thioether.
22 . The platinum (II) complex of claim 1 , wherein at least two of Y 1 ′-Y 4 ′ are NR 18 .