IP Library Granted Patent US 9,040,749
Granted Patent B2
US 9,040,749 · App. 14/006,078 · Granted May 26, 2015

Borazine derivatives

Inventors: Davide Bonifazi (Reggio Emilia, IT); Simon Kervyn De Meerendre (Autre-Eglise, BE); Franco Cacialli (London, IT); Oliver Fenwick (London, GB)
Assignees: UNIVERSITE DE NAMUR; UCL BUSINESS PLC
H01L51/005C07F5/05H01L51/008H01L51/5012H01L51/5032
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Quick Facts
Patent No.
US 9,040,749
App. No.
14/006,078
Granted
May 26, 2015
Kind
B2
Abstract

Borazine derivatives are used in the manufacture of electronic devices, in particular electroluminescent and semiconductor devices. More specifically, stable borazine derivatives include boron atoms substituted by aryl groups used in one or more layers of an electroluminescent or a semiconductor device, in particular in the emissive layer of organic light-emitting devices (OLED).

Claims (22)

1. A borazine derivative represented by the following formula:

wherein the substituents R 4 to R 18 are the same or different from each other;

wherein each of R 4 to R 18 is independently selected from the group consisting of: hydrogen; linear or branched saturated alkyl group; linear or branched unsaturated alkyl group; cycloalkyl group; aryl group; aralkyl group; heteroaryl group; acyl group; hydroxyl; alkoxy group; aryloxy group; acyloxy group; amino group; alkylamino group; arylamino group; acylamino group; cyano group; carboxyl group; thio group; aminocarbonyl group; carbamoyl group, aryloxycarbonyl group, phenoxycarbonyl group, alkoxycarbonyl group and halogen;

wherein R 4 , R 8 , R 9 , R 13 , R 14 and R 18 cannot simultaneously be selected to be hydrogen;

wherein R 4 to R 8 and R 14 to R 18 cannot simultaneously be selected to be fluorine;

wherein the substituents R 19 to R 27 are the same or different from each other;

wherein each of R 19 to R 27 is independently selected from the group consisting of:

hydrogen; linear or branched saturated alkyl group; linear or branched unsaturated alkyl group; cycloalkyl group; aryl group; aralkyl group; heteroaryl group; acyl group; hydroxyl; alkoxy group; aryloxy group; acyloxy group; amino group; alkylamino group; arylamino group; acylamino group; cyano group; carboxyl group; thio group; aminocarbonyl group; carbamoyl group, aryloxycarbonyl group, phenoxycarbonyl group, alkoxycarbonyl group and halogen;

wherein at least one substituent selected from the group of R 6 , R 11 and R 16 is independently selected from the group consisting of linear or branched saturated alkyl groups; and

wherein at least two substituents selected from the group of R 4 , R 8 , R 9 , R 13 , R 14 and R 18 are independently selected from the group consisting of linear saturated alkyl groups and branched saturated alkyl groups.

2. A derivative according to claim 1 , wherein at least one substituent selected from the group of R 22 , R 23 , R 24 , R 25 , R 26 and R 27 is independently selected to be hydrogen.

3. A derivative according to claim 1 , wherein at least one substituent selected from the group of R 19 , R 20 and R 21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups.

4. A derivative according to claim 1 , able to emit in the UV region with a quantum yield above 0.05.

5. A derivative according to claim 1 , wherein at least one substituent selected from the group of R 6 , R 11 and R 16 is independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 6 carbon atoms.

6. A derivative according to claim 1 , wherein at least one substituent selected from the group of R 6 , R 11 and R 16 is independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 4 carbon atoms.

7. A derivative according to claim 1 , wherein at least one substituent selected from the group of R 6 , R 11 and R 16 is independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 3 carbon atoms.

8. A derivative according to claim 1 , wherein at least two substituents selected from the group of R 4 , R 8 , R 9 , R 13 , R 14 and R 18 are independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 6 carbon atoms.

9. A derivative according to claim 1 , wherein at least two substituents selected from the group of R 4 , R 8 , R 9 , R 13 , R 14 and R 18 are independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 4 carbon atoms.

10. A derivative according to claim 1 , wherein at least two substituents selected from the group of R 4 , R 8 , R 9 , R 13 , R 14 and R 18 are independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 3 carbon atoms.

11. A derivative according to claim 3 , wherein at least one substituent selected from the group of R 19 , R 20 and R 21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups with 1 to 12 carbon atoms.

12. A derivative according to claim 3 , wherein at least one substituent selected from the group of R 19 , R 20 and R 21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups with 1 to 6 carbon atoms.

13. A derivative according to claim 3 , wherein at least one substituent selected from the group of R 19 , R 20 and R 21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups with 1 to 3 carbon atoms.

Assignments (3)
CORRECTIVE ASSIGNMENT TO ADD THE SECOND ASSIGNOR PREVIOUSLY RECORDED AT REEL: 032118 FRAME: 0914. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Apr 22, 2015
From: BONIFAZI, DAVIDE; KERVYN DE MEERENDRE, SIMON; CACIALLI, FRANCO; FENWICK, OLIVER
To: FACULTES UNIVERSITAIRES NOTRE-DAME DE LA PAIX; UCL BUSINESS PLC
Reel/Frame 035487/0838 →
CHANGE OF NAME Recorded Jul 24, 2014
From: FACULTES UNIVERSITAIRES NOTRE-DAME DE LA PAIX
To: UNIVERSITE DE NAMUR
Reel/Frame 033408/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2014
From: BONIFAZI, DAVIDE; KERVYN DE MEERENDRE, SIMON; CACIALLI, FRANCO; FENWICK, OLIVER
To: FACULTES UNIVERSITAIRES NOTRE-DAME DE LA PAIX
Reel/Frame 032118/0914 →
Priority Claims (1)
EP 11158909 · Mar 18, 2011 · regional
Continuity (1)
Related Publication 20140088324A1 · Mar 27, 2014