Organic ionic compounds, compositions and electronic devices

Patent metadata

Field	Value
Publication number	US-9496502-B2
Application number	US-201214117049-A
Country	US
Kind code	B2
Filing date	Apr 18, 2012
Priority date	May 12, 2011
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

The present invention relates inter alia to novel compositions, compounds and formulations of multi-charged organic cations or anions having a functional organic group or a non-functional organic group. The present invention further relates to devices comprising the these compositions, compounds or formulations.

First claim

The invention claimed is:

1. A composition comprising at least one non-polymeric organic ionic compound and at least one non-ionic organic functional compound, wherein the organic ionic compound is a compound of formula (1):
( M ) m+/− y ×( N ) n−/+   Formula (1);

wherein:
M is an organic ion having the charge m+ or m−;
N is an organic or inorganic counter ion being the same or different at each occurrence having the charge n− or n+;
m indicates the number of the charge of M and is an integer of ≧2;
y indicates the number of N, and is an integer of ≧1;
n indicates the number of the charge of N and is an integer of ≧1;
wherein the net charge of the compound of formula (1) is zero;
and wherein the non-ionic organic functional compound is selected from the group consisting of host materials, phosphorescent emitters, fluorescent emitters, hole transporting materials (HTM), hole injecting materials (HIM), electron transporting materials (ETM), and electron injecting materials (EIM).

2. The composition of claim 1 , wherein the composition comprises a non-ionic fluorescent and/or phosphorescent emitter and a non-ionic host material.

3. The composition of claim 1 , wherein (M) m+/− in the compound of formula (1) is a non-functional ion, i.e. is not a fluorescence or phosphorescence emitter, not a host, not a hole injecting material, not a hole transporting material, not an electron injecting material or not an electron transporting material.

4. The composition of claim 1 , wherein (M) m+/− in the compound of formula (1) comprises an aliphatic hydrocarbyl group.

5. The composition of claim 1 , wherein (M) m+/− comprises a functional organic group selected from a fluorescence emitting group, a host group, a hole injecting or transporting group, and an electron injecting or transporting group.

6. The composition of claim 1 , wherein (M) m+/− has a molecular weight in the range from 6 to 1000 g/mol.

7. The composition of claim 1 , wherein M is a cation and N is selected from [HSO 4 ] − , [SO 4 ] 2− , [NO 3 ] − , [BF 4 ] − , [(R F )BF 3 ] − , [(R F ) 2 BF 2 ] − , [(R F ) 3 BF] − , [(R F ) 4 B] − , [B(CN) 4 ] − , [PO 4 ] 3− , [HPO 4 ] 2− , [H 2 PO 4 ] − , [Alkyl-OPO 3 ] 2− , [(Alkyl-O) 2 PO 2 ] − , [Alkyl-PO 3 ] 2− , [R F PO 3 ] 2− , [(Alkyl) 2 PO 2 ] − , [(R F ) 2 PO 2 ] − , [R F SO 3 ] − , [HOSO 2 (CF 2 ) k SO 2 O] − , [OSO 2 (CF 2 ) k SO 2 O] 2− , [Alkyl-SO 3 ] − , [HOSO 2 (CH 2 ) k SO 2 O] − , [OSO 2 (CH 2 ) k SO 2 O] 2− , [Alkyl-OSO 3 ] − , [Alkyl-C(O)O] − , [HO(O)C(CH 2 ) k C(O)O] − , [R F C(O)O] − , [HO(O)C(CF 2 ) k C(O)O] − , [O(O)C(CF 2 ) k C(O)O] 2− , [(R F SO 2 ) 2 N] − , [(FSO 2 ) 2 N] − , [((R F ) 2 P(O)) 2 N] − , [(R F SO 2 ) 3 C] − , [(FSO 2 ) 3 C] − , PF 6 − , [PF 3 (C 2 F 5 ) 3 ] − , [PF 3 (CF 3 ) 3 ] − , [B(COOCOO) 2 − , [(CF 3 SO 2 ) 2 N] − , [(C 2 F 5 SO 2 ) 2 N] − , [(CF 3 SO 2 )(C 4 F 9 SO 2 )N] − , [(CN) 2 N] − , [CF 3 SO 2 ] 3 C] − , and [(CN) 3 C] − ; wherein k is an integer from 1 to 8; R F is a fluorinated aryl or alkyl-aryl or a fluorinated alkyl of formula (C o F 2o−x+1 H x ), wherein o is an integer from 1 to 12 and x is an integer of from 0 to 7.

8. The composition of claim 1 , wherein M is an anion and N is selected from K + , Na + , Li + , ammonium-, phosphonium-, thiouronium-, thioxonium-, guanidinium-cations, heterocylic cations, and derivatives thereof.

9. The composition of claim 1 , wherein m is 2 or 3, y is 3 or 2 and n is 2 or 1.

10. The composition of claim 1 , wherein the composition further comprises at least one ion conductor compound.

11. The composition of claim 1 , wherein the composition further comprises at least one dye.

12. A non-polymeric functional ionic organic compound selected from host materials, phosphorescent emitters, fluorescent emitters, hole transporting materials (HTM), hole injecting materials (HIM), electron transporting materials (ETM), and electron injecting materials (EIM), having a formula (1):
( M ) m+/− y ×( N ) n−/+   Formula (1);

wherein
N is an organic or inorganic counter ion being the same or different at each occurrence having the charge n− or n+;
m indicates the number of the charge of M and is an integer of ≧2;
y indicates the number of N, and is an integer of ≧1;
n indicates the number of the charge of N and is an integer of ≧1;
(M) m+/− comprises a functional organic group selected from a fluorescence emitting group, a host group, a hole injecting or transporting group, and an electron injecting or transporting group, and has a molecular weight in the range from 6 to 1000 g/mol;
wherein the molecular weight of the compound of formula (1) is below 1000 g/mol; and
wherein the net charge of the compound of formula (1) is zero.

13. A formulation comprising:
the compound of claim 12 or a composition comprising at least one non-polymeric organic ionic compound and at least one non-ionic organic functional compound, wherein the organic ionic compound is a compound of formula (1):
( M ) m+/− y ×( N ) n−/+   Formula (1);

wherein:
M is an organic ion having the charge m+ or m−;
N is an organic or inorganic counter ion being the same or different at each occurrence having the charge n− or n+;
m indicates the number of the charge of M and is an integer of ≧2;
y indicates the number of N, and is an integer of ≧1;
n indicates the number of the charge of N and is an integer of ≧1;
wherein the net charge of the compound of formula (1) is zero;
and wherein the non-ionic organic functional compound is selected from the group consisting of host materials, phosphorescent emitters, fluorescent emitters, hole transporting materials (HTM), hole injecting materials (HIM), electron transporting materials (ETM), and electron injecting materials (EIM);
and at least one solvent.

14. An electronic device comprising at least one compound according to claim 12 or a composition comprising at least one non-polymeric organic ionic compound and at least one non-ionic organic functional compound, wherein the organic ionic compound is a compound of formula (1):
( M ) m+/− y ×( N ) n−/+   Formula (1);

wherein:
M is an organic ion having the charge m+ or m−;
N is an organic or inorganic counter ion being the same or different at each occurrence having the charge n− or n+;
m indicates the number of the charge of M and is an integer of ≧2;
y indicates the number of N, and is an integer of ≧1;
n indicates the number of the charge of N and is an integer of ≧1;
wherein the net charge of the compound of formula (1) is zero;
and wherein the non-ionic organic functional compound is selected from the group consisting of host materials, phosphorescent emitters, fluorescent emitters, hole transporting materials (HTM), hole injecting materials (HIM), electron transporting materials (ETM), and electron injecting materials (EIM).

15. The electronic device of claim 14 , wherein the device is an organic electroluminescent device, or an organic sensor, or an organic solar cell.

16. The electronic device of claim 14 , wherein the device is selected from organic light emitting diodes (OLED), polymer light emitting diodes (PLED), organic light emitting transistors (OLET), organic light emitting electrochemical cells (OLEC), organic light emitting electrochemical transistors (OLEETs), organic field effect transistors (OFET), thin film transistors (TFT), organic solar cells (O-SC), organic laser diodes (O-laser), organic integrated circuits (O-IC), radio frequency identification (RFID) tags, photodetector, sensors, logic circuits, memory elements, capacitor, charge injection layers, Schottky diodes, planarisi

Assignees

• Pan Junyou
• Parham Amir Hossain
• Merck Patent Gmbh

Inventors

• Pan Junyou
• Parham Amir Hossain

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• A61N5/0616

  Skin treatment other than tanning · CPC title

• H01L51/0052

  Electricity · mapped topic

• H01L51/0058 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic