IP Library Granted Patent US 8,603,642
Granted Patent B2
US 8,603,642 · App. 12/465,235 · Granted Dec 10, 2013

Internal connector for organic electronic devices

Inventors: Tukaram K. Hatwar (Penfield, NY); Jeffrey P. Spindler (Rochester, NY); Denis Y. Kondakov (Kendall, NY); Steven A. Van Slyke (Pittsford, NY); Sven Z. Murano (Dresden, DE); Gufeng He (Dreseden, DE)
Assignee: Global OLED Technology LLC
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Quick Facts
Patent No.
US 8,603,642
App. No.
12/465,235
Granted
Dec 10, 2013
Kind
B2
Abstract

The invention provides an electronic device including an anode and a cathode, between which there are at least two organic phototransducing units where the units are separated by an intermediate connecting region which comprises in sequence: an organic p-type layer, an intermediate layer in direct contact with the organic p-type layer and including a compound that has a LUMO more negative than −3.0 eV and is different from the organic compound in the organic p-type layer, and an n-type doped organic layer in direct contact with the intermediate layer and including an electron transport material as a host and an organic n-dopant with a HOMO less negative than −4.5 eV. In one embodiment, the electronic device is a tandem OLED.

Claims (30)

1. An electronic device comprising an anode and a cathode, between which there are at least two organic phototransducing units where the units are separated by an intermediate connecting region which comprises:

a) an organic p-type layer;

b) an intermediate layer in direct contact with the organic p-type layer consisting essentially of a single compound that has a LUMO more negative than −3.0 eV and is different from an organic compound in the organic p-type layer; and

c) an organic n-type doped layer in direct contact with the intermediate layer and including an electron transport material as a host and an organic n-dopant with an effective HOMO less negative than −4.5 eV.

2. The device of claim 1 wherein the organic n-dopant has an effective HOMO less negative than −3.5 eV.

3. The device of claim 1 wherein the n-dopant is selected from 2,2′-Diisopropyl -1,1′,3,3′-tetramethyl-2,2′,3,3′,4,4′,5,5′,6,6′,7,7′-dodecahydro-2,2′-bibenzo [d]imidazole (NDR-1); 4,4′,5,5′-Tetracyclohexyl-1,1′,2,2′,3,3′-hexamethyl-2,2′,3,3′-tetrahydro -2,2′-biimidazole (NDR-2); 2,2′-diisopropyl-4,4′,5,5′-tetrakis(2-methoxyphenyl)-1,1′,3,3′-tetramethyl-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biimidazole (NDR-3); 2,2′-diisopropyl-1,1′,3,3′-tetramethyl-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-bibenzo[d]imidazole (NDR-4);

2,2′-diisopropyl-4,4′,5,5′-tetrakis(3-methoxyphenyl)-1,1′,3,3′-tetramethyl-2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biimidazole (NDR-5); 2-Isopropyl-1,3-dimethyl-2,3,6,7-tetrahydro-5,8-dioxa-1,3-diaza -cyclopenta[b]naphthene; Bis-[1,3-dimethyl-2-isopropyl-1,2-dihydro-benzimidazolyl-(2)];

and 2,2′-Diisopropyl-4,5-bis (2-methoxyphenyl)-4′,5′bis(4-methoxyphenyl)-1,1′,3,3′-tetramethyl -2,2′,3,3′tetrahydro-2,2′-biimidazole.

4. The device of claim 1 wherein the organic p-type layer is a p-type doped layer including an aromatic tertiary amine as a host and a p-type dopant with a LUMO more negative than -4.5 eV.

5. The device of claim 4 wherein the p-type dopant is chosen from hexaazatriphenylene compounds, fluorinated derivatives of tetracyanobenzoquinonedimethane or radialenes.

6. The device of claim 1 wherein the intermediate layer includes a metal phthalocyanine.

7. A tandem OLED comprising an anode and a cathode, between which there are at least two electroluminescent units where the units are separated by an intermediate connecting region which comprises:

a) an organic p-type layer;

b) an intermediate layer in direct contact with the organic p-type layer, consisting essentially of a single compound that has a LUMO more negative than −3.0 eV and is different from an organic compound in the organic p-type layer; and

c) an organic n-type doped layer in direct contact with the intermediate layer and including an electron transport material as a host and an organic n-dopant with an effective HOMO less negative than −4.5 eV.

8. The tandem OLED of claim 7 wherein white light is emitted.

9. The tandem OLED of claim 7 wherein the organic p-type layer includes one or more compounds selected from the group consisting of 2,2′-(perfluorocyclohexa-2,5-diene-1,4-diylidene) dimalononitrile (TCNQ-1); N′-Dicyan-2,3,5,6-tetrafluoro-1,4-chinondiimine; N,N′-Dicyan-2,5-dichloro-1,4-chinondiimine; N,N′-Dicyan-2,5-dichloro -3,6-difluoro-1,4-chinondiimine; N,N′-Dicyan-2,3,5,6,7,8-hexafluoro-1,4-naphthochinondiimine; 1,4,5,8-Tetrahydro-1,4,5,8-tetrathia-2,3,6,7-tetracyanoanthrachinone;

1,3,4,5,7,8-Hexafluoronaphtho-2,6-chinontetracyanomethane (TCNQ-7); 2,2′-(2,5-Dibrom-3,6-difluorcyclohexa -2,5-dien-1,4-diyliden)dimalononitrile; 4,4′-(1E,1′E)-(2-cyano-3,6-difluoro-5-isocyanocyclohexa -2,5-diene-1,4-diylidene)bis(cyanomethan-1-yl-1-ylidene)bis(2,3,5,6-tetrafluorobenzonitrile); 2,2′,2″-(Cyclopropan-1,2,3- triyliden)tris(2-(2,6-dichlor-3,5-difluor-4-(trifluormethyl)phenyl)acetonitrile); (2E,2′E,2″E)-2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(perfluorophenyl) acetonitrile); 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(perfluorobiphenyl-4-yl)acetonitrile); 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(2,6-dichloro-3,5-difluoro-4-(trifluoromethyl) phenyl)-acetonitrile);and Benzeneacetonitrile, α,α′ ,α″-1,2,3-cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorol].

10. The tandem OLED of claim 7 wherein the electron transporting material as a host in the organic n-type doped layer is chosen from metal oxinoids, anthracenes, rubrenes, fluoranthenes or phenanthrolines.

11. The tandem OLED of claim 7 wherein the organic p-type layer consists essentially of a hexaaztriphenylene compound.

12. The tandem OLED of claim 7 wherein the organic p-type layer is an organic p-type doped layer including an aromatic tertiary amine as a host and a p-dopant with a LUMO more negative than −4.5 eV.

13. The tandem OLED of claim 12 wherein the p-dopant is chosen from hexaazatriphenylene compounds, fluorinated derivatives of cyanobenzoquinonedimethanes or radialenes.

14. The tandem OLED of claim 12 wherein p-dopant in the p-type doped layer is chosen from fluorinated derivatives of tetracyanobenzoquinonedimethane or radialenes and the intermediate layer consists essentially of a hexaazatriphenylene compound.

15. The tandem OLED of claim 14 wherein the hexaazatriphenylene compound in the intermediate layer is:

16. The tandem OLED of claim 7 wherein the intermediate layer includes a metal phthalocyanine.

17. The tandem OLED of claim 16 wherein the metal phthalocyanine is copper phthalocyanine.

18. A solar cell comprising an anode and a cathode, between which there are at least two organic photoactive units where the units are separated by an intermediate connecting region which comprises:

a) an organic p-type layer;

b) an intermediate layer in direct contact with the organic p-type layer consisting essentially of a single compound that has a LUMO more negative than −3.0 eV and is different from an organic compound in the organic p-type layer; and

c) an organic n-type doped layer in direct contact with the intermediate layer and including an electron transport material as a host and an organic n-dopant with an effective HOMO less negative than −4.5 eV.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2010
From: EASTMAN KODAK COMPANY
To: GLOBAL OLED TECHNOLOGY LLC
Reel/Frame 024831/0480 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2009
From: HATWAR, TUKARAM K.; SPINDLER, JEFFREY P.; KONDAKOV, DENIS Y.; VAN SLYKE, STEVE A.; MURANO, SVEN Z.; HE, GUFEND
To: EASTMAN KODAK COMPANY; NOVALED AG
Reel/Frame 022814/0066 →
Continuity (1)
Related Publication 20100288362A1 · Nov 18, 2010