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US 2018/0019396 A1Published application
Amino Phosphazene Bases As N-Dopants In Organic Electronics
AssigneeSiemens Aktiengesellschaft
InventorsFlorian KESSLER, Stefan REGENSBURGER, Guenter SCHMID
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Abstract
The present invention relates to n-dopants for doping organic electron transport materials, wherein the n-dopants have at least one aminophosphazene group of formula 1 having 4 nitrogen atoms bonded to a phosphorus atom.
Claims30
1-15. (canceled)
A method for producing an n-conducting organic-electrical layer, the method comprising:
- depositing a n-dopant comprising at least one aminophosphazene group of the formula
- with an organic electron transport material, the organic electron transport material selected from the group consisting of 2,2′,2″-(1,3,5-benzinetriyl)tris(1-phenyl-1-H-benzimidazole), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole;
- 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 8-hydroxyquinolinolatolithium;
- 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole;
- 1,3-bis[2-(2,2′-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]benzene;
- 4,7-diphenyl-1,10-phenanthroline (Bphen);
- 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole;
- bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminum;
- 6,6′-bis[5-(biphenyl-4-yl)-1,3,4-oxadiazo-2-yl]-2,2′-bipyridyl;
- 2-phenyl-9,10-di(naphthalen-2-yl)anthracene;
- 2,7-bis[2-(2,2′-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]-9,9-dimethylfluorene;
- 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene;
- 2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline;
- 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline;
- tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane;
- 1-methyl-2-(4-(naphthalen-2-yl)phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline;
- phenyldipyrenylphosphine oxide;
- 3,3′,5,5′-tetra[(m-pyridyl)phen-3-yl]biphenyl;
- 1,3,5-tris[(3-pyridyl)phen-3-yl]benzene;
- 4,4′-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl;
- 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene;
- diphenylbis(4-(pyridin-3-)phenyl)silane;
- 3,5-di(pyren-1-yl)pyridine;
- 1,3,5-tri(p-pyrid-3-ylphenyl)benzene;
- 2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine;
- naphthalenetetracarboxylic dianhydride and its imides;
- perylenetetracarboxylic dianhydride and its imides;
- and materials based on siloles, having a silacyclopentadiene unit, and
- forming an n-conducting organic-electrical layer comprising a n-dopant volume % thickness concentration of ≧0.01% and ≦30%.
26 more elements
A method for producing n-conducting organic-electrical layers, characterized in that an n-dopant of formula
- wherein substituents R1 to R4 independently of one another are selected from the group of R consisting of a bond, H, D, C1-C60 saturated or unsaturated alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl;
- and C1-C60 aryl, alkylaryl, heteroaryl;
- substituent R5 is selected from NR2 and [—N═P(NR2)2—]n wherein n=1 to 5;
- and
- substituent R6 is selected from the group of R and [—P(NR2)2═N—]n where n=1 to 5, optionally the substituents independently of one another may be joined to form cyclic units;
- wherein the dopant is a compound having a noncyclic aminophosphazene scaffold;
- and
- the dopant is deposited together with an organic electron transport material within a layer, and the n-dopant and the electron transport material are reacted.
5 more elements
A method for producing an n-conducting organic-electrical layer, the method comprising:
- depositing a n-dopant comprising ≧2 and ≦7 aminophosphazene groups of the formula
- with an organic electron transport material to form an n-conducting organic-electrical layer comprising a n-dopant volume % thickness concentration of ≧0.01% and ≦30%.
Dependencies are inferred from the claim text.