Electronic device and compound

• US 10,403,824 B2
• Filed: 07/03/2015
• Issued: 09/03/2019
• Est. Priority Date: 07/04/2014
• Status: Active Grant

• Current Assignee: Novaled GmbH
• Original Assignee: Novaled GmbH
• Inventors: Dorok, Sascha, Steudtner, Ina, Heggemann, Ulrich, Runge, Steffen, Klose, Manuela
• Primary Examiner(s): McGinty, Douglas J
• Application Number:
  US15/323,905
• Publication Number:
  US 20170155047A1
• Time in Patent Office: 1,523 Days
• Field of Search: 252500, 429188, 429189
• CPC Class Codes: C07C 211/53 having the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino groups
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 279/18 having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 233/50 with carbocyclic radicals directly attached to said nitrogen atoms
• CPC Class Codes: C07D 235/30 Nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 295/125 with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
• CPC Class Codes: C07D 295/13 to an acyclic saturated chain
• CPC Class Codes: C08G 73/02 Polyamines
• CPC Class Codes: C08G 73/026 Wholly aromatic polyamines
• CPC Class Codes: H10K 30/20 comprising organic-organic junctions, e.g. donor-acceptor junctions
• CPC Class Codes: H10K 30/30 comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
• CPC Class Codes: H10K 30/57 comprising multiple junctions, e.g. tandem PV cells
• CPC Class Codes: H10K 30/81 Electrodes
• CPC Class Codes: H10K 71/30 Doping active layers, e.g. electron transporting layers
• CPC Class Codes: H10K 85/211 Fullerenes, e.g. C60
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/656 comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

The invention relates to an electronic device comprising a compound having Formula (1): AB_x (1), wherein A is a structural moiety that consists of at least two atoms and comprises a conjugated system of delocalized electrons, each B is independently selected from an imine functional group (1a), wherein R¹, R², R³, R⁴ are independently selected from C₁-C₃₀ alkyl, C₂-C₃₀ alkenyl, C₂-C₃ alkinyl, C₃-C₃₀ cycloalkyl, C₆-C₃₀ aryl, C₂-C₃₀ heteroaryl, C₇-C₃₀ arylalkyl, C₃-C₃₀ heteroarylalkyl, the wave line represents a covalent bond to the imine nitrogen atom, G is in each group (1a) independently selected from a quarternary carbon atom and from a cyclopropenylidene structural moiety, x is an integer equal one or higher, preferably equal two or higher, and the lone electron pair of the imine nitrogen atom and/or the pi-electrons of the imine double bond of at least one group B is conjugated with the conjugated system of delocalized electrons comprised in the structural moiety A, with the proviso that two or more of the substituents R¹, R², R³, R⁴ may be connected to form a ring that may contain also unsaturation and, if any of the substituents R¹, R², R³, R⁴ comprises two or more carbon atoms, up to one third of the overall count of the carbon atoms in the substituent or in any ring formed by two connected substituents can be replaced with heteroatoms independently selected from O, S, N and B as well as to an electrically semiconducting material and a compound for use in the electronic device.

Claims

1. Organic electronic device comprising a compound having Formula 1

AB_x 

 

(1),

wherein

A is a structural moiety that consists of at least two atoms and comprises a conjugated system of delocalized electrons,

each B is independently selected from an imine functional group (Ia)

2. Organic electronic device according to claim 1, wherein x is an integer selected from 2, 3 and 4 and the lone electron pairs of the imine nitrogen atoms and/or the pi-electrons of the imine double bonds of at least two groups B are conjugated with the conjugated system of delocalized electrons comprised in the structural moiety A.

3. Organic electronic device according to claim 1, wherein A is a C₃-C₄₀ arene or C₂-C₄₀ heteroarene structural moiety that contains one conjugated system of delocalized electrons.

4. Organic electronic device according to claim 1, wherein A is a C₆-C₁₈ arene or C₄-C₁₈ heteroarene structural moiety and the lone electron pairs of the imine nitrogen atoms and/or the pi-electrons of the imine double bonds of all groups B are conjugated with the conjugated system of delocalized electrons comprised in the structural moiety A.

5. Organic electronic device according to claim 1, having a layered structure comprising several layers.

6. Organic electronic device according to claim 5, wherein the layer comprising the compound of Formula 1 is an electron transport layer or an electron injection layer.

7. Organic electronic device according to claim 5, wherein the layer comprising the compound of Formula 1 is an electron transport layer comprising an electron transport matrix and having a thickness of more than 50 nm, or a neat layer having a thickness less than 5 nm.

8. Organic electronic device according to claim 5, wherein the layer comprising the compound of Formula 1 is in direct contact to an electrode.

9. Organic electronic device according to claim 5, wherein a layer comprising the compound of Formula 1 is in direct contact to an electron transport layer.

10. Organic electronic device according to claim 5, wherein the layer comprising the compound of Formula 1 is part of a pn-junction connecting a light absorbing unit to an additional light absorbing unit in a tandem device or in a multiple stacked device and/or a pn-junction connecting a cathode or an anode to a light absorbing unit.

11. Organic electronic device according to claim 6, wherein the layer comprising the compound of Formula 1 is an electron transport layer comprising an electron transport matrix and having a thickness of more than 50 nm, or a neat layer having a thickness less than 5 nm.

12. Organic electronic device comprising:

a layered structure, wherein the layered structure comprises (i) an anode, (ii) a cathode, and (iii) a layer comprising an n-dopant arranged between the anode and the cathode;

wherein the n-dopant comprises a compound having Formula 1

AB_x 

 

(1),

wherein

A is a structural moiety that consists of at least two atoms and comprises a conjugated system of delocalized electrons,

each B is independently selected from an imine functional group (Ia)

13. Organic electronic device according to claim 12, wherein x is an integer selected from 2, 3 and 4 and the lone electron pairs of the imine nitrogen atoms and/or the pi-electrons of the imine double bonds of at least two groups B are conjugated with the conjugated system of delocalized electrons comprised in the structural moiety A.

14. Organic electronic device according to claim 12, wherein A is a C₃-C₄₀ arene or C₂-C₄₀ heteroarene structural moiety that contains one conjugated system of delocalized electrons.

15. Organic electronic device according to claim 12, wherein A is a C₆-C₁₈ arene or C₄-C₁₈ heteroarene structural moiety and the lone electron pairs of the imine nitrogen atoms and/or the pi-electrons of the imine double bonds of all groups B are conjugated with the conjugated system of delocalized electrons comprised in the structural moiety A.

16. Organic electronic device according to claim 12, wherein the layer comprising the n-dopant is an electron transport layer or an electron injection layer.

17. Organic electronic device according to claim 12, wherein the layer comprising the n-dopant is an electron transport layer comprising an electron transport matrix and having a thickness of more than 50 nm, or a neat layer having a thickness less than 5 nm.

18. Organic electronic device according to claim 12, wherein the layer comprising the n-dopant is in direct contact to the anode or the cathode.

19. Organic electronic device according to claim 12, further comprising an electron transport layer, wherein the layer comprising the n-dopant is in direct contact to the electron transport layer.

20. Organic electronic device according to claim 12, further comprising a light absorbing unit, wherein the layer comprising the n-dopant is part of a pn-junction connecting the light absorbing unit to an additional light absorbing unit in a tandem device or in a multiple stacked device and/or a pn-junction connecting the cathode or the anode to the light absorbing unit.