Transparent electroluminescent devices with controlled one-side emissive displays

Abstract

A light emitting device includes a transparent organic light emitting device and a quarter-wave plate. The transparent organic light emitting device includes a chiral complex emitter and produces circularly polarized light, and the quarter-wave plate converts the circularly polarized light into linearly polarized light. Generating linearly polarized light includes generating circularly polarized light via a transparent organic light emitting device including a chiral complex emitter, and passing the circularly polarized light through a quarter-wave plate to yield linearly polarized light.

Claims

1. A light emitting device comprising: a transparent organic light emitting device; and a single optically active light-blocking element comprising: a linear polarizer; and a quarter-wave plate, wherein the transparent organic light emitting device comprises a chiral complex emitter that produces circularly polarized light, the quarter-wave plate converts the circularly polarized light into linearly polarized light, and the linear polarizer filters the linearly polarized light, and wherein the chiral complex emitter, the quarter-wave plate, and the linear polarizer are configured to allow transmission of light, generated by the transparent organic light emitting device and within the transparent organic light emitting device, through a single side of the light emitting device.

2. The light emitting device of claim 1, wherein the chiral complex emitter has a structure represented by General Formula IA: ##STR00009## wherein: M represents Pt.sup.2+, Pd.sup.2+, Ir.sup.+, Rh.sup.+, or Au.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; Y.sup.1a represents O; S; NR.sup.3a, wherein R.sup.3a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.3b).sub.2, wherein each R.sup.3b in (R.sup.3b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.3c).sub.2, wherein each R.sup.3c in (R.sup.3c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.5a, or CR.sup.5b, wherein each of R.sup.5a and R.sup.5b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents C; N; O; S; NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.6c).sub.2, wherein Z is C or Si, and each R.sup.6c in (R.sup.6c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; m is 1 or 2; n is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e is a chiral center.

3. The light emitting device of claim 1, wherein the chiral complex emitter has a structure represented by General Formula IB: ##STR00010## wherein: M represents Pt.sup.2+, Pd.sup.2+, Ir.sup.+, Rh.sup.+, or Au.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; Y.sup.1a represents O; S; NR.sup.3a, wherein R.sup.3a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.3b).sub.2, wherein each R.sup.3b in (R.sup.3b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.3c).sub.2, wherein each R.sup.3c in (R.sup.3c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1c represents O; S; NR.sup.5a, wherein R.sup.5a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.5b).sub.2, wherein each R.sup.5b in (R.sup.5b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.5c).sub.2, wherein each R.sup.5c in (R.sup.5c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino12; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.7a or CR.sup.7b, as permitted by valency, wherein each of R.sup.7a and R.sup.7b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.7c).sub.2, wherein Z is C or Si, and each R.sup.7c in (R.sup.7c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; m is 1 or 2; n is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e is a chiral center.

4. The light emitting device of claim 1, wherein the chiral complex emitter has a structure represented by General Formula IIA: ##STR00011## wherein: M represents Ir.sup.3+or Rh.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.3a, or CR.sup.3b, as permitted by valency, wherein each of R.sup.3a and R.sup.3b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents C; N; O; S; NR.sup.4a or CR.sup.4b, as permitted by valency, wherein each of R.sup.4a and R.sup.4b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.4c).sub.2, wherein Z is C or Si, and each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e, valency permitting, independently represents C; N, O, S, NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; l is 1 or 2; m is 1 or 2; n is 1 or 2; o is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; at least one of M, R.sup.1, R.sup.2, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e is a chiral center.

5. The light emitting device of claim 4, wherein: two adjacent R.sup.1 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent R.sup.2 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; R.sup.1 or R.sup.2 together with an adjacent R.sup.3a or R.sup.3b form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.3c, Y.sup.3d, Y.sup.3e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.4c, Y.sup.4d, and Y.sup.4e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.5c, Y.sup.5d, and Y.sup.5e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2a and Y.sup.3d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2d and Y.sup.4d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; or Y.sup.6d and Y.sup.5d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl.

6. The light emitting device of claim 4, wherein the chiral complex emitter has a structure selected from one of the following structures: ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059##

7. The light emitting device of claim 1, wherein the chiral complex emitter has a structure represented by General Formula IIB: ##STR00060## wherein: M represents Ir.sup.3+or Rh.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.1a, Y.sup.1c, and Y.sup.1d independently represents O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each of R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.5a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.5b).sub.2, wherein each R.sup.5b in (R.sup.5b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.5c).sub.2, wherein each R.sup.5c in (R.sup.5c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1e is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.6c).sub.2, wherein Z is C or Si, and each R.sup.6c in (R.sup.6c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e, valency permitting, independently represents N, O, S, NR.sup.6a, or CR.sup.6b as permitted by valency; wherein each m is independently 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.1d, Y.sup.1e, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, Y.sup.6e is a chiral center.

8. The light emitting device of claim 7, wherein: two adjacent R.sup.1 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent R.sup.2 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; R.sup.1 or R.sup.2 together with an adjacent R.sup.4a or R.sup.4b form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.3c, Y.sup.3d, Y.sup.3e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.6a, Y.sup.6d, and Y.sup.6e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.5b, Y.sup.5c, and Y.sup.5e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.4d and Y.sup.4e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2a and Y.sup.3d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2d and Y.sup.4d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl; Y.sup.4e and Y.sup.5e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl; or Y.sup.5c and Y.sup.6d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl.

9. A method of generating linearly polarized light, the method comprising: generating circularly polarized light via a transparent organic light emitting device comprising a chiral complex emitter; passing the circularly polarized light through a single optically active light-blocking element comprising a quarter-wave plate and a linear polarizer, wherein a difference between a refractive index of the quarter-wave plate in a first direction and a refractive index of the quarter-wave plate in a second direction perpendicular to the first direction is in a range of 0.1 to 0.2, wherein the chiral complex emitter, the quarter-wave plate, and the linear polarizer are configured to allow transmission of light, generated by the transparent organic light emitting device and within the transparent organic light emitting device, through a single side of the light emitting device.

10. The method of claim 9, wherein the chiral complex emitter has a structure represented by General Formula IA: ##STR00061## wherein: M represents Pt.sup.2+, Pd.sup.2+, Ir.sup.+, Rh.sup.+, or Au.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; Y.sup.1a represents O; S; NR.sup.3a, wherein R.sup.3a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.3b).sub.2, wherein each R.sup.3b in (R.sup.3b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.3c).sub.2, wherein each R.sup.3c in (R.sup.3c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.5a or CR.sup.5b, as permitted by valency, wherein each of R.sup.5a and R.sup.5b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents C; N; O; S; NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.6c).sub.2, wherein Z is C or Si, and each R.sup.6c in (R.sup.6c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; m is 1 or 2; n is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e is a chiral center.

11. The method of claim 9, wherein the chiral complex emitter has a structure represented by General Formula IB: ##STR00062## wherein: M represents Pt.sup.2+, Pd.sup.2+, Ir.sup.+, Rh.sup.+, or Au.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; Y.sup.1a represents O; S; NR.sup.3a, wherein R.sup.3a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.3b).sub.2, wherein each R.sup.3b in (R.sup.3b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.3c).sub.2, wherein each R.sup.3c in (R.sup.3c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1c represents O; S; NR.sup.5a, wherein R.sup.5a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.5b).sub.2, wherein each R.sup.5b in (R.sup.5b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.5c).sub.2, wherein each R.sup.5c in (R.sup.5c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.7a or CR.sup.7b, as permitted by valency, wherein each of R.sup.7a and R.sup.7b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.7c).sub.2, wherein Z is C or Si, and each R.sup.7c in (R.sup.7c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; m is 1 or 2; n is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e is a chiral center.

12. The method of claim 9, wherein the chiral complex emitter has a structure represented by General Formula IIA: ##STR00063## wherein: M represents Ir.sup.3+or Rh.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.3a or CR.sup.3b, as permitted by valency, wherein each of R.sup.3a and R.sup.3b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents C; N; O; S; NR.sup.4a or CR.sup.4b, as permitted by valency, wherein each of R.sup.4a and R.sup.4b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.4c).sub.2, wherein Z is C or Si, and each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e, valency permitting, independently represents C; N, O, S, NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; m is 1 or 2; n is 1 or 2; l is 1 or 2; o is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; at least one of M, R.sup.1, R.sup.2, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e is a chiral center.

13. The method of claim 12, wherein: two adjacent R.sup.1 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent R.sup.2 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; R.sup.1 or R.sup.2 together with an adjacent R.sup.3a or R.sup.3b form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.3c, Y.sup.3d, Y.sup.3e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.4c, Y.sup.4d, and Y.sup.4e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.5c, Y.sup.5d, and Y.sup.5e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2a and Y.sup.3d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2d and Y.sup.4d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl; Y.sup.6d and Y.sup.5d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl.

14. The method of claim 12, wherein the chiral complex emitter has a structure selected from one of the following structures: ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103##

15. The method of claim 9, wherein the chiral complex emitter has a structure represented by General Formula IIB: ##STR00104## wherein: M represents Ir.sup.3+or Rh.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.1a, Y.sup.1c, and Y.sup.1d independently represents O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each of R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.5a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.5b).sub.2, wherein each R.sup.5b in (R.sup.5b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.5c).sub.2, wherein each R.sup.5c in (R.sup.5c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1e is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents C or N or NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.6a or CR.sup.6b, as permitted by valency, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.6c).sub.2, wherein Z is C or Si, and each R.sup.6c in (R.sup.6c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e, valency permitting, independently represents N, O, S, NR.sup.6a, or CR.sup.6b as permitted by valency; wherein each m is independently 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.1d, Y.sup.1e, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, Y.sup.6e is a chiral center.

16. The method of claim 15, wherein: two adjacent R.sup.1 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent R.sup.2 form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; R.sup.1 or R.sup.2 together with an adjacent R.sup.4a or R.sup.4b form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.3c, Y.sup.3d, Y.sup.3e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.6a, Y.sup.6d, and Y.sup.6e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; two adjacent Y.sup.5b, Y.sup.5c, and Y.sup.5e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.4d and Y.sup.4e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2a and Y.sup.3d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl; Y.sup.2d and Y.sup.4d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl; Y.sup.4e and Y.sup.5e form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl; or Y.sup.5c and Y.sup.6d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl.

17. The light emitting device of claim 1, wherein the absorptive linear polarizer has a polarization ratio greater than 100,000:1.

18. The light emitting device of claim 1, wherein the absorptive linear polarizer comprises elongated silver nanoparticles embedded in glass plates.

19. The light emitting device of claim 1, wherein the quarter-wave plate retards light having a wavelength of 560 nm light.

20. The light emitting device of claim 1, wherein the single side of the light emitting device is opposite the linear polarizer.

21. The light emitting device of claim 1, wherein the light emitting device is configured to allow transmission of ambient light from both sides of the light emitting device.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 depicts an organic light emitting device (OLED).

(2) FIGS. 2A and 2B depict linearly polarized and circularly polarized light waves, respectively.

(3) FIGS. 3A and 3B depict chiral isomers of an octahedral metal complex.

(4) FIGS. 4A-4D depict structures with chiral centers.

(5) FIGS. 5A-5D depict general schemes for chiral metal complex based emitters.

(6) FIG. 6A depicts a transparent OLED with selected circularly polarized emission.

(7) FIG. 6B depicts a transparent OLED with selected circularly polarized emission with polarizers on one side.

(8) FIGS. 7-16 show chemical structures of selected iridium chiral octahedral complexes.

DETAILED DESCRIPTION

(9) The present disclosure can be understood more readily by reference to the following detailed description and Examples.

(10) Before the present compounds, devices, and/or methods are disclosed and described, it is to be understood that they are not limited to specific synthetic methods unless otherwise specified, or to particular reagents unless otherwise specified, as such can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing, example methods and materials are now described.

(11) As used in the specification and the appended claims, the singular forms a, an, and the include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a component includes mixtures of two or more components.

(12) As used herein, the terms optional or optionally means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.

(13) Disclosed are the components to be used to prepare the compositions described herein as well as the compositions themselves to be used within the methods disclosed herein. These and other materials are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these materials are disclosed that while specific reference of each various individual and collective combinations and permutation of these compounds cannot be explicitly disclosed, each is specifically contemplated and described herein. For example, if a particular compound is disclosed and discussed and a number of modifications that can be made to a number of molecules including the compounds are discussed, specifically contemplated is each and every combination and permutation of the compound and the modifications that are possible unless specifically indicated to the contrary. Thus, if a class of molecules A, B, and C are disclosed as well as a class of molecules D, E, and F and an example of a combination molecule, A-D is disclosed, then even if each is not individually recited each is individually and collectively contemplated meaning combinations, A-E, A-F, B-D, B-E, B-F, C-D, C-E, and C-F are considered disclosed. Likewise, any subset or combination of these is also disclosed. Thus, for example, the sub-group of A-E, B-F, and C-E would be considered disclosed. This concept applies to all aspects of this application including, but not limited to, steps in methods of making and using the compositions. Thus, if there are a variety of additional steps that can be performed it is understood that each of these additional steps can be performed with any specific embodiment or combination of embodiments of the methods.

(14) As referred to herein, a linking atom or group can connect two atoms such as, for example, an N atom and a C atom. A linking atom or group is in one aspect disclosed as Y.sup.1a, Y.sup.1b, Y.sup.1c and/or Y.sup.1d herein. The linking atom can optionally, if valency permits, have other chemical moieties attached. For example, in one aspect, an oxygen would not have any other chemical groups attached as the valency is satisfied once it is bonded to two groups (e.g., N and/or C groups). In another aspect, when carbon is the linking atom, two additional chemical moieties can be attached to the carbon. Suitable chemical moieties include amine, amide, thiol, aryl, heteroaryl, cycloalkyl, and heterocyclyl moieties.

(15) As used herein, the term substituted is contemplated to include all permissible substituents of organic compounds. In a broad aspect, the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. The permissible substituents can be one or more and the same or different for appropriate organic compounds. For purposes of this disclosure, the heteroatoms, such as nitrogen, can have hydrogen substituents and/or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatoms. This disclosure is not intended to be limited in any manner by the permissible substituents of organic compounds. Also, the terms substitution or substituted with include the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g., a compound that does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc. It is also contemplated that, in certain aspects, unless expressly indicated to the contrary, individual substituents can be further (i.e., further substituted or unsubstituted).

(16) The term alkyl as used herein is a branched or unbranched saturated hydrocarbon group of 1 to 24 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, s-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. The alkyl group can be cyclic or acyclic. The alkyl group can be branched or unbranched. The alkyl group can also be substituted or unsubstituted. For example, the alkyl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or thiol, as described herein. A lower alkyl group is an alkyl group containing from one to six (e.g., from one to four) carbon atoms.

(17) Throughout the specification alkyl is generally used to refer to both unsubstituted alkyl groups and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying the specific substituent(s) on the alkyl group. For example, the term halogenated alkyl or haloalkyl specifically refers to an alkyl group that is substituted with one or more halide, e.g., fluorine, chlorine, bromine, or iodine. The term alkoxyalkyl specifically refers to an alkyl group that is substituted with one or more alkoxy groups, as described below. The term alkylamino specifically refers to an alkyl group that is substituted with one or more amino groups, as described below, and the like. When alkyl is used in one instance and a specific term such as alkylalcohol is used in another, it is not meant to imply that the term alkyl does not also refer to specific terms such as alkylalcohol and the like.

(18) This practice is also used for other groups described herein. That is, while a term such as cycloalkyl refers to both unsubstituted and substituted cycloalkyl moieties, the substituted moieties can, in addition, be specifically identified herein; for example, a particular substituted cycloalkyl can be referred to as, e.g., an alkylcycloalkyl. Similarly, a substituted alkoxy can be specifically referred to as, e.g., a halogenated alkoxy, a particular substituted alkenyl can be, e.g., an alkenylalcohol, and the like. Again, the practice of using a general term, such as cycloalkyl, and a specific term, such as alkylcycloalkyl, is not meant to imply that the general term does not also include the specific term.

(19) The term cycloalkyl as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and the like. The term heterocycloalkyl is a type of cycloalkyl group as defined above, and is included within the meaning of the term cycloalkyl, where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkyl group and heterocycloalkyl group can be substituted or unsubstituted. The cycloalkyl group and heterocycloalkyl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or thiol as described herein.

(20) The terms alkoxy and alkoxyl as used herein to refer to an alkyl or cycloalkyl group bonded through an ether linkage; that is, an alkoxy group can be defined as OA.sup.1 where A.sup.1 is alkyl or cycloalkyl as defined above. Alkoxy also includes polymers of alkoxy groups as just described; that is, an alkoxy can be a polyether such as OA.sup.1OA.sup.2 or OA.sup.1(OA.sup.2).sub.aOA.sup.3, where a is an integer of from 1 to 200 and A.sup.1, A.sup.2, and A.sup.3 are alkyl and/or cycloalkyl groups.

(21) The term alkenyl as used herein is a hydrocarbon group of from 2 to 24 carbon atoms with a structural formula containing at least one carbon-carbon double bond. Asymmetric structures such as (A.sup.1A.sup.2)CC(A.sup.3A.sup.4) are intended to include both the E and Z isomers. This can be presumed in structural formulae herein wherein an asymmetric alkene is present, or it can be explicitly indicated by the bond symbol CC. The alkenyl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol, as described herein.

(22) The term cycloalkenyl as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms and containing at least one carbon-carbon double bound, i.e., CC. Examples of cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, norbornenyl, and the like. The term heterocycloalkenyl is a type of cycloalkenyl group as defined above, and is included within the meaning of the term cycloalkenyl, where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkenyl group and heterocycloalkenyl group can be substituted or unsubstituted. The cycloalkenyl group and heterocycloalkenyl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol as described herein.

(23) The term alkynyl as used herein is a hydrocarbon group of 2 to 24 carbon atoms with a structural formula containing at least one carbon-carbon triple bond. The alkynyl group can be unsubstituted or substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol, as described herein.

(24) The term cycloalkynyl as used herein is a non-aromatic carbon-based ring composed of at least seven carbon atoms and containing at least one carbon-carbon triple bound. Examples of cycloalkynyl groups include, but are not limited to, cycloheptynyl, cyclooctynyl, cyclononynyl, and the like. The term heterocycloalkynyl is a type of cycloalkenyl group as defined above, and is included within the meaning of the term cycloalkynyl, where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkynyl group and heterocycloalkynyl group can be substituted or unsubstituted. The cycloalkynyl group and heterocycloalkynyl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol as described herein.

(25) The term aryl as used herein is a group that contains any carbon-based aromatic group including, but not limited to, benzene, naphthalene, phenyl, biphenyl, phenoxybenzene, and the like. The term aryl also includes heteroaryl, which is defined as a group that contains an aromatic group that has at least one heteroatom incorporated within the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. Likewise, the term non-heteroaryl, which is also included in the term aryl, defines a group that contains an aromatic group that does not contain a heteroatom. The aryl group can be substituted or unsubstituted. The aryl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol as described herein. The term biaryl is a specific type of aryl group and is included in the definition of aryl. Biaryl refers to two aryl groups that are bound together via a fused ring structure, as in naphthalene, or are attached via one or more carbon-carbon bonds, as in biphenyl.

(26) The term aldehyde as used herein is represented by the formula C(O)H. Throughout this specification C(O) is a short hand notation for a carbonyl group, i.e., CO.

(27) The terms amine or amino as used herein are represented by the formula NA.sup.1A.sup.2, where A.sup.1 and A.sup.2 can be, independently, hydrogen or alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.

(28) The term alkylamino as used herein is represented by the formula NH(-alkyl) where alkyl is described herein. Representative examples include, but are not limited to, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, (sec-butyl)amino group, (tert-butyl)amino group, pentylamino group, isopentylamino group, (tert-pentyl)amino group, hexylamino group, and the like.

(29) The term dialkylamino as used herein is represented by the formula N(-alkyl).sub.2 where alkyl is a described herein. Representative examples include, but are not limited to, dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, diisobutylamino group, di(sec-butyl)amino group, di(tert-butyl)amino group, dipentylamino group, diisopentylamino group, di(tert-pentyl)amino group, dihexylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-ethyl-N-propylamino group and the like.

(30) The term carboxylic acid as used herein is represented by the formula C(O)OH.

(31) The term ester as used herein is represented by the formula OC(O)A.sup.1 or C(O)OA.sup.1, where A.sup.1 can be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein. The term polyester as used herein is represented by the formula -(A.sup.1O(O)C-A.sup.2-C(O)O).sub.a or -(A.sup.1O(O)C-A.sup.2-OC(O)).sub.a, where A.sup.1 and A.sup.2 can be, independently, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group described herein and a is an integer from 1 to 500. Polyester is as the term used to describe a group that is produced by the reaction between a compound having at least two carboxylic acid groups with a compound having at least two hydroxyl groups.

(32) The term ether as used herein is represented by the formula A.sup.1OA.sup.2, where A.sup.1 and A.sup.2 can be, independently, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group described herein. The term polyether as used herein is represented by the formula -(A.sup.1O-A.sup.2O).sub.a, where A.sup.1 and A.sup.2 can be, independently, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group described herein and a is an integer of from 1 to 500. Examples of polyether groups include polyethylene oxide, polypropylene oxide, and polybutylene oxide.

(33) The term halide as used herein refers to the halogens fluorine, chlorine, bromine, and iodine.

(34) The term heterocyclyl, as used herein refers to single and multi-cyclic non-aromatic ring systems and heteroaryl as used herein refers to single and multi-cyclic aromatic ring systems: in which at least one of the ring members is other than carbon. The terms includes azetidine, dioxane, furan, imidazole, isothiazole, isoxazole, morpholine, oxazole, oxazole, including, 1,2,3-oxadiazole, 1,2,5-oxadiazole and 1,3,4-oxadiazole, piperazine, piperidine, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidine, tetrahydrofuran, tetrahydropyran, tetrazine, including 1,2,4,5-tetrazine, tetrazole, including 1,2,3,4-tetrazole and 1,2,4,5-tetrazole, thiadiazole, including, 1,2,3-thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole, thiazole, thiophene, triazine, including 1,3,5-triazine and 1,2,4-triazine, triazole, including, 1,2,3-triazole, 1,3,4-triazole, and the like.

(35) The term hydroxyl as used herein is represented by the formula OH.

(36) The term ketone as used herein is represented by the formula A.sup.1C(O)A.sup.2, where A.sup.1 and A.sup.2 can be, independently, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.

(37) The term azide as used herein is represented by the formula N.sub.3.

(38) The term nitro as used herein is represented by the formula NO.sub.2.

(39) The term nitrile as used herein is represented by the formula CN.

(40) The term silyl as used herein is represented by the formula -SiA.sup.1A.sup.2A.sup.3, where A.sup.1, A.sup.2, and A.sup.3 can be, independently, hydrogen or an alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.

(41) The term sulfo-oxo as used herein is represented by the formulas S(O)A.sup.1, S(O).sub.2A.sup.1, OS(O).sub.2A.sup.1, or OS(O).sub.2OA.sup.1, where A.sup.1 can be hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein. Throughout this specification S(O) is a short hand notation for SO. The term sulfonyl is used herein to refer to the sulfo-oxo group represented by the formula S(O).sub.2A.sup.1, where A.sup.1 can be hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein. The term sulfone as used herein is represented by the formula A.sup.1S(O).sub.2A.sup.2, where A.sup.1 and A.sup.2 can be, independently, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein. The term sulfoxide as used herein is represented by the formula A.sup.1S(O)A.sup.2, where A.sup.1 and A.sup.2 can be, independently, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.

(42) The term thiol as used herein is represented by the formula SH.

(43) As used herein, the term absent that defines a variable, e.g., Y.sup.1b, means that the variable is not present such that the two groups connected through the variable are not bonded to each other. For example, in A.sup.1-Y.sup.1b-A.sup.2, when Y.sup.1b is absent, A.sup.1 and A.sup.2 are not connected to each other.

(44) R.sup.1, R.sup.2, R.sup.3, R.sup.n, where n is an integer, as used herein can, independently, possess one or more of the groups listed above. For example, if R.sup.1 is a straight chain alkyl group, one of the hydrogen atoms of the alkyl group can optionally be substituted with a hydroxyl group, an alkoxy group, an alkyl group, a halide, and the like. Depending upon the groups that are selected, a first group can be incorporated within second group or, alternatively, the first group can be pendant (i.e., attached) to the second group. For example, with the phrase an alkyl group comprising an amino group, the amino group can be incorporated within the backbone of the alkyl group. Alternatively, the amino group can be attached to the backbone of the alkyl group. The nature of the group(s) that is (are) selected will determine if the first group is embedded or attached to the second group.

(45) Compounds described herein may contain optionally substituted moieties. In general, the term substituted, whether preceded by the term optionally or not, means that one or more hydrogens of the designated moiety are replaced with a suitable substituent. Unless otherwise indicated, an optionally substituted group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be substituted with more than one substituent selected from a specified group, the substituent may be either the same or different at every position. Combinations of substituents envisioned by this invention are preferably those that result in the formation of stable or chemically feasible compounds. In is also contemplated that, in certain aspects, unless expressly indicated to the contrary, individual substituents can be further optionally substituted (i.e., further substituted or unsubstituted).

(46) The use of chiral metal complex emitters will eliminate the potential photon loss due to the polarizers by generating the corresponding polarized electroluminescent spectra. In addition, the specific alignment of chiral metal complex emitters may also reduce the plasimon quenching from the metal electrode and enhance the outcoupling efficiency of the device (i.e., more photons will exit from the device to produce higher illumination intensity).

(47) A chiral structure, such as a molecule or organometallic complex, is not superimposable on its mirror image. FIGS. 3A and 3B depict chiral isomers of an octahedral metal complex. A chiral center is an atom in a structure, such as an organic molecule, that has four or more unique atoms or groups attached to it.

(48) General schemes of chiral metal complex emitters are depicted in presented in FIGS. 4A-D. In FIGS. 4A and 4B, the iridium is a chiral center. In FIG. 4C, the platinum is a chiral center. In FIG. 4D, the carbon is a chiral center. FIGS. 4A-4C depict three classes of chiral metal complexes. FIG. 4A depicts an octahedral metal complex with three different cyclometalating ligands (e.g., Ir(CN)(CN)(CN)). FIG. 4B depicts an octahedral metal complex with two different cyclometalating ligands (i.e., Ir(CN).sub.2(CN)). FIG. 4C depicts a non-planar asymmetric tetrahedral metal complex.

(49) FIGS. 5A-5D depict general schemes for chiral metal complex based emitters, where at least one of M or other functional group such as C, C, C, N, N, and N includes one or more chiral centers.

(50) FIGS. 6A and 6B provide an illustration of a transparent OLED with selected circularly polarized emission without (FIG. 6A) and with (FIG. 6B) with a polarizer on one side. As depicted in FIG. 6A, transparent OLED 600 produces the selected circularly polarized emission observable from both sides of the OLED. FIG. 6B depicts light emitting device 610. Light emitting device 610 includes transparent OLED 600 and quarter-wave plate 612. In some cases, light emitting device 610 includes linear polarizer 614. As depicted in FIG. 6B, the exclusively circularly polarized light from OLED 600 is converted to the exclusively linearly polarized light after passing through quarter-wave plate 612. The resulting linearly polarized light may be filtered by linear polarizer 614.

(51) Quarter-wave plate 612 may include a quarter-wave film including a thin anisotropic film, whose refractive index in one direction is higher than that of the other, perpendicular axis. Generally, the difference of refractive index is in the range of 0.1-0.2, but may vary based on material. For a film whose refractive index difference between the x and y axes is 0.2 and has a thickness of 0.7 m, applied to quarter-wave film, the retardation is 140 nm (0.2700 nm), which is suitable for a quarter-wave film for 560 nm wavelength light. Typically, a commercialized OLED panel uses a quarter-wave film having a retardation around 140 nm, which will also include 100 m of protective layer, such as cellulose triacetate film (TAC), applied to the both sides of the quarter-wave film.

(52) Linear polarizer 614 may belong to one of two general categories: absorptive polarizers, where the unwanted polarization states are absorbed by the device, and beam-splitting polarizers, where the unpolarized beam is split into two beams with opposite polarization state. One type of absorptive polarizer is made of elongated silver nanoparticles embedded in thin (0.5 mm) glass plates. These polarizers are durable, and typically polarize light better than plastic Polaroid film, achieving polarization ratios as high as 100,000:1 and absorption of correctly polarized light as low as 1.5%. Beam-splitting polarizers split the incident beam into two beams of differing linear polarization. For an ideal polarizing beamsplitter, these would be fully polarized, with orthogonal polarizations. For many common beam-splitting polarizers, however, only one of the two output beams is fully polarized. The other contains a mixture of polarization states. For one-sided transparent display application, absorptive polarizers are typically a more cost-effective choice.

(53) The chiral metal complexes described herein may be used in transparent electroluminescent devices to achieve controlled one-side emissive displays.

(54) A first class of chiral complex emitters has a structure represented by General Formula IA:

(55) ##STR00005##
wherein: M represents Pt.sup.2+, Pd.sup.2+, Ir.sup.+, Rh.sup.+, or Au.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; Y.sup.1a represents O; S; NR.sup.3a, wherein R.sup.3a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.3b).sub.2, wherein each R.sup.3b in (R.sup.3b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.3c).sub.2, wherein each R.sup.3c in (R.sup.3c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents N, NR.sup.6a, or CR.sup.6b, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.7a or CR.sup.7b, wherein each of R.sup.7a and R.sup.7b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.7c).sub.2, wherein Z is C or Si, and each R.sup.7c in (R.sup.7c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; l is 1 or 2; m is 1 or 2; n is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e is a chiral center.

(56) Implementations of General Formula IA may include one or more of the following bonding arrangements in which two of R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e and Y.sup.4e with the proper valency form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl. In some examples, two adjacent R.sup.1; two adjacent R.sup.2; R.sup.1 or R.sup.2 together with an adjacent R.sup.3a or R.sup.3b; R.sup.1 or R.sup.2 together with an adjacent R.sup.6a or R.sup.6b; two adjacent Y.sup.3c, Y.sup.3d, and Y.sup.3e; two adjacent Y.sup.4c, Y.sup.4d, and Y.sup.4e; Y.sup.2a and Y.sup.3d; or Y.sup.2d and Y.sup.4d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl.

(57) A second class of chiral complex emitters has a structure represented by General Formula IB:

(58) ##STR00006##
wherein: M represents Pt.sup.2+, Pd.sup.2+, Ir.sup.+, Rh.sup.+, or Au.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; Y.sup.1a represents O; S; NR.sup.3a, wherein R.sup.3a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.3b).sub.2, wherein each R.sup.3b in (R.sup.3b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.3c).sub.2, wherein each R.sup.3c in (R.sup.3c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1c represents O; S; NR.sup.5a, wherein R.sup.5a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.5b).sub.2, wherein each R.sup.5b in (R.sup.5b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.5c).sub.2, wherein each R.sup.5c in (R.sup.5c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents N, NR.sup.6a, or CR.sup.6b, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.7a or CR.sup.7b, wherein each of R.sup.7a and R.sup.7b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.7c).sub.2, wherein Z is C or Si, and each R.sup.7c in (R.sup.7c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; m is 1 or 2; n is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e is a chiral center.

(59) Implementations of General Formula IB may include one or more of the following bonding arrangements in which two of R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e with the proper valency form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl. In some examples, two adjacent R.sup.1; two adjacent R.sup.2; R.sup.1 or R.sup.2 together with an adjacent R.sup.3a or R.sup.3b; R.sup.1 or R.sup.2 together with an adjacent R.sup.6a or R.sup.6b; two adjacent Y.sup.3c, Y.sup.3d, and Y.sup.3e; two adjacent Y.sup.4c, Y.sup.4d, and Y.sup.4e; Y.sup.2a and Y.sup.3d; or Y.sup.2d and Y.sup.4d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl.

(60) A third class of chiral metal complex emitters is represented by General Formula IIA:

(61) ##STR00007##
wherein: M represents Ir.sup.3+or Rh.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents N, NR.sup.3a, or CR.sup.3b, wherein each of R.sup.3a and R.sup.3b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.4a or CR.sup.4b, wherein each of R.sup.4a and R.sup.4b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.4c).sub.2, wherein Z is C or Si, and each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e, valency permitting, independently represents N, O, S, NR.sup.6a or CR.sup.6b, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; l is 1 or 2; m is 1 or 2; n is 1 or 2; is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e is a chiral center.

(62) In some examples, Y.sup.2b and Y.sup.2c represent N. In other examples, each of Y.sup.2a and Y.sup.2d independently represents NR.sup.3a or CR.sup.3b. In some cases, one of Y.sup.2a and Y.sup.2b is NR.sup.3a and the other is CR.sup.3b.

(63) In some examples, each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e independently represents N, O, S, NR.sup.4a, or CR.sup.4b. In certain examples, each of Y.sup.3a, Y.sup.3b, Y.sup.3cY.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e independently represents N, NR.sup.4a, or CR.sup.4b.

(64) In some embodiments, each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e independently represents N, O, NR.sup.6a, or CR.sup.6b. In some embodiments, each of Y.sup.5a, Y.sup.5b, Y.sup.5cY.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e independently represents N, NR.sup.6a, or CR.sup.6b.

(65) Implementations of General Formula IIA may include one or more of the following bonding arrangements in which two of R.sup.1, R.sup.2, Y.sup.3a, Y.sup.3b, Y.sup.2a, Y.sup.2d, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5c, Y.sup.5d, Y.sup.5e and Y.sup.6d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl. In some examples, two adjacent R.sup.1; two adjacent R.sup.2; R.sup.1 or R.sup.2 together with an adjacent R.sup.3a or R.sup.3b; two adjacent Y.sup.3c, Y.sup.3d, and Y.sup.3e; two adjacent Y.sup.4c, Y.sup.4d, and Y.sup.4e; two adjacent Y.sup.5c, Y.sup.5d, Y.sup.5e; Y.sup.2a and Y.sup.3d; Y.sup.2d and Y.sup.4d; or Y.sup.6d and Y.sup.5d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl.

(66) In some examples, Y.sup.2b and Y.sup.2c represent N. In other examples, each of Y.sup.2a and Y.sup.2d independently represents NR.sup.3a or CR.sup.3b. In some cases, one of Y.sup.2a and Y.sup.2b is NR.sup.3a and the other is CR.sup.3b.

(67) In some examples, each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e independently represents N, O, S, NR.sup.4a, or CR.sup.4b. In some examples, each of Y.sup.3a, Y.sup.3b, Y.sup.3cY.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e independently represents N, NR.sup.4a, or CR.sup.4b.

(68) In some embodiments, each of Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e independently represents N, O, NR.sup.6a, or CR.sup.6b. In some embodiments, each of Y.sup.5a, Y.sup.5bY.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e independently represents N, NR.sup.6a, or CR.sup.6b.

(69) FIGS. 7-16 show chemical structures of selected chiral octahedral Ir based complexes based on the third class of chiral emissive materials.

(70) A fourth class of chiral complex emitter has a structure represented by General Formula IIB:

(71) ##STR00008##
wherein: M represents Ir.sup.3+or Rh.sup.3+; each R.sup.1 and R.sup.2 in (R.sup.1).sub.2 and (R.sup.2).sub.2 independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.1a, Y.sup.1c, and Y.sup.1d independently represents O; S; NR.sup.4a, wherein each of R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.4c).sub.2, wherein each R.sup.4c in (R.sup.4c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1b is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.5a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.5b).sub.2, wherein each R.sup.5b in (R.sup.5b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or C(R.sup.5c).sub.2, wherein each R.sup.5c in (R.sup.5c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Y.sup.1e is present or absent, and if present, represents a covalent bond or O; S; NR.sup.4a, wherein R.sup.4a represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; Si(R.sup.4b).sub.2, wherein each R.sup.4b in (R.sup.4b).sub.2 independently represents substituted or unsubstituted C.sub.1-C.sub.4 alkyl; each of Y.sup.2a, Y.sup.2b, Y.sup.2c, and Y.sup.2d, valency permitting, independently represents N, NR.sup.6a, or CR.sup.6b, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted: C.sub.1-C.sub.4 alkyl or amino; each of Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, and Y.sup.4e, valency permitting, independently represents N; O; S; NR.sup.6a or CR.sup.6b, wherein each of R.sup.6a and R.sup.6b independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; or Z(R.sup.6c).sub.2, wherein Z is C or Si, and each R.sup.6c in (R.sup.6c).sub.2 independently represents hydrogen or substituted or unsubstituted C.sub.1-C.sub.4 alkyl; l is 1 or 2; m is 1 or 2; n is 1 or 2; is 1 or 2; the open dotted circle indicates partial or full unsaturation of the ring with which it is associated; and at least one of M, R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.1d, Y.sup.1e, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, Y.sup.6e is a chiral center.

(72) Implementations of General Formula IIB may include one or more of the following bonding arrangements in which two of R.sup.1, R.sup.2, Y.sup.1a, Y.sup.1b, Y.sup.1c, Y.sup.1d, Y.sup.1e, Y.sup.2a, Y.sup.2b, Y.sup.2c, Y.sup.2d, Y.sup.3a, Y.sup.3b, Y.sup.3c, Y.sup.3d, Y.sup.3e, Y.sup.4a, Y.sup.4b, Y.sup.4c, Y.sup.4d, Y.sup.4e, Y.sup.5a, Y.sup.5b, Y.sup.5c, Y.sup.5d, Y.sup.5e, Y.sup.6a, Y.sup.6b, Y.sup.6c, Y.sup.6d, and Y.sup.6e with the proper valency form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl. In some examples, two adjacent R.sup.1; two adjacent R.sup.2; R.sup.1 or R.sup.2 together with an adjacent R.sup.4a or R.sup.4b; two adjacent Y.sup.3c, Y.sup.3d, and Y.sup.3e; two adjacent Y.sup.6a, Y.sup.6d, and Y.sup.6e; two adjacent Y.sup.5b, Y.sup.5c, and Y.sup.5e; Y.sup.4d, and Y.sup.4e; Y.sup.2a and Y.sup.3d; Y.sup.2d and Y.sup.4d; Y.sup.4e and Y.sup.5e; or Y.sup.5c and Y.sup.6d form a substituted or unsubstituted: carbocyclyl, aryl, heterocyclyl, or heteroaryl.

(73) A number of embodiments of the invention have been described. Nevertheless, it will be understood that various modifications may be made without departing from the spirit and scope of the invention. Accordingly, other embodiments are within the scope of the following claims.