IP Library Granted Patent US 9,502,660
Granted Patent B2
US 9,502,660 · App. 14/126,331 · Granted Nov 22, 2016

Electronic device and compound

Inventors: Sascha Dorok (Dresden, DE); Ulrich Heggemann (Dresden, DE); Ina Faltin (Dresden, DE); Manuela Klose (Dresden, DE); Rudolf Lessmann (Duesseldorf, DE)
Assignee: NOVALED GMBH
H01L51/0059B82Y10/00C07F9/065C07F9/5355H01L51/005H01L51/0046H01L51/4253Y02E10/549
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Quick Facts
Patent No.
US 9,502,660
App. No.
14/126,331
Granted
Nov 22, 2016
Kind
B2
Abstract

The present invention relates to an electronic device comprising a compound according to formula 1 A-B (1) and wherein —Ar 1 is a C6-C18 arylene, which can be monocyclic or polycyclic and may be optionally substituted by one or more C 1 -C 10 -alkyl or C 3 -C 10 -cycloalkyl groups, —Ar 2 is a C6-C18 arene skeleton, optionally substituted with electron donating groups R 4 , —B 1 and B 2 are independently selected from B and Ar 2 , —B 3 is independently selected from the same group as B, —R 1 , R 2 , R 3 are independently selected from alkyl, arylalkyl, cycloalkyl, aryl, dialkylamino, - x is selected from 0, 1, 2 and 3, wherein for x>1 each Ar 1 may be different, - y is a non-zero integer up to the overall count of valence sites on the arene skeleton, - z is a integer from zero up to the overall count of valence sites on the arene skeleton minus y; as well as a respective compound according to formula A-B.

Claims (40)

1. An electronic device comprising an n-dopant according to formula 1:

A-B   (1), wherein

and wherein

Ar 1 is a C6-C18 arylene,

Ar 2 is a C6-C18 arene skeleton, and R 4 is selected independently from electron donating groups,

B 1 and B 2 are independently selected from B or Ar 2 ,

B 3 is independently selected from the same group as B,

R 1 , R 2 , and R 3 are independently selected from alkyl, arylalkyl, cycloalkyl, aryl, or dialkylamino,

x is selected from 0, 1, 2 or 3, wherein when x>1 each Ar 1 may be different,

y is a non-zero integer up to the overall count of valence sites on the arene skeleton, and

z is a integer from zero up to the overall count of valence sites on the arene skeleton minus y.

2. The electronic device according to claim 1 , wherein any of R 1 , R 2 , and R 3 is independently selected from

straight or branched, saturated or unsaturated C1-C24 alkyl,

saturated or unsaturated C3-C24 cycloalkyl or alkyl comprising at least one cyclic structure,

C6-C24 aryl, wherein the overall count of carbon atoms includes also any possible substitution by a single substituent or more substituents selected from saturated or unsaturated, straight or branched alkyl or cycloalkyl, aryl, arylalkyl or alkylaryl groups and within this substitution up to three alkyl groups can be attached to the arene core by an ether linkage or up to six alkyl groups can be attached through a disubstituted nitrogen atom,

C7-C25 arylalkyl, wherein the overall C atom count includes also a possible substitution on the arene ring or rings and within this substitution up to three alkyl groups can be attached to the arene ring or rings through an ether linkage or up to six alkyl groups through a disubstituted nitrogen atom,

C2-C24 dialkylamino, wherein the alkyl groups may be the same or different, straight or branched, may include also alicyclic or aromatic structures or be unsaturated with a provision that the carbon atom bearing a double or triple bond is not adjacent to nitrogen, the two alkyls in the dialkylamino group may be so linked that they form a cycle comprising the nitrogen atom and up to four ether linkages can be included between methylene groups of the dialkylamino group, and with a provision that in any case the nitrogen and/or oxygen atoms are separated by at least two carbon atoms,

or two groups selected from R 1 -R 3 may be linked so that they form a cyclic structure including a phosphorus atom.

3. The electronic device according to claim 2 , wherein any of R 1 , R 2 , and R 3 is independently selected from C1-C4 alkyl, C3-C10 cycloalkyl, C7-C10 arylalkyl, C6-C14 aryl, or C2-C12 dialkylamino.

4. The electronic device according to claim 1 , wherein

Ar 2 is a benzene or naphthalene skeleton,

Ar 1 is phenylene, or x is 0,

y is selected from 1, 2, 3 or 4 if Ar 2 is benzene, or from 1, 2, 3, 4, 5, or 6 if Ar 2 is naphthalene, and

z is selected from 0 or 1 if Ar 2 is benzene, or from 0, 1, or 2 if Ar 2 is naphthalene.

5. The electronic device according to claim 4 , wherein

Ar 2 is a benzene skeleton, and

Ar 1 is 1,4-phenylene or x is 0.

6. The electronic device according to claim 1 , wherein each of R 1 -R 3 is independently selected from methyl, isopropyl, tert-butyl, cyclohexyl, phenyl, tolyl, xylyl, mesityl, naphthyl, anthryl, phenanthryl, 1,1′-biphenyl-yl, 1,3-diisopropylphenyl, benzyl, 4-methoxybenzyl, or dimethylamino.

7. The electronic device according to claim 1 , wherein the device has a layered structure comprising several layers.

8. The electronic device according to claim 7 , wherein a layer comprising the n-dopant of Formula 1 is an electron transport layer.

9. The electronic device according to claim 7 , wherein a layer comprising the n-dopant of Formula 1 has a thickness of less than 5 nm.

10. The electronic device according to claim 7 , wherein the layer comprising the n-dopant of Formula 1 is in direct contact to an electrode.

11. The electronic device according to claim 7 , wherein a layer comprising the n-dopant of Formula 1 is in direct contact to an electron transport layer.

12. The electronic device according to claim 7 , wherein a layer comprising the n-dopant of Formula 1 is part of a connecting unit, the connecting unit comprising a pn-junction connecting a first light absorbing unit to a second light absorbing unit in a tandem device or a multiple stacked device.

13. The electronic device according to claim 1 , wherein the device is a solar cell.

14. The electronic device according to claim 1 , wherein each R 4 is independently selected from alkyl, alkoxy, aryl, or aryloxy having an overall count of carbon atoms in the range of C1-C22.

15. The electronic device according to claim 14 , wherein each R 4 is independently selected from methyl, methoxy, ethyl, ethoxy, propyl, propoxy, isopropyl, isopropoxy, butyl, butoxy, tert-butyl, tert.-butoxy, cyclohexyl, benzyl, or benzyloxy.

16. The electronic device according to claim 2 , wherein up to four ether linkages can be included within any of the C3-C24 alkyl or cycloalkyl structures with a provision that oxygen atoms are in any case separated by at least two carbon atoms.

17. The electronic device according to claim 10 , wherein the electrode is a cathode.

18. The electronic device according to claim 1 , wherein Ar 1 is a polycyclic C8-C18 arylene that is substituted by one or more C1-C10-alkyl or C3-C10-cycloalkyl groups.

Assignments (2)
CHANGE OF NAME Recorded Oct 11, 2016
From: NOVALED AG
To: NOVALED GMBH
Reel/Frame 040315/0818 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2014
From: DOROK, SASCHA; HEGGEMANN, ULRICH; FALTIN, INA; KLOSE, MANUELA; LESSMANN, RUDOLF
To: NOVALED AG
Reel/Frame 032450/0404 →
Priority Claims (1)
EP 11170945 · Jun 22, 2011 · regional
Continuity (1)
Related Publication 20140182681A1 · Jul 3, 2014