Organic light-emitting diode materials

Patent metadata

Field	Value
Publication number	US-9972795-B2
Application number	US-201515310241-A
Country	US
Kind code	B2
Filing date	May 13, 2015
Priority date	May 14, 2014
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

Described herein are molecules for use in organic light emitting diodes. Example molecules comprise at least one moiety A and at least one moiety D. Values and preferred values of the moieties A and D are described herein. The molecules comprise at least one atom selected from Si, Se, Ge, Sn, P, or As.

First claim

What is claimed is:

1. A compound represented by any one of the following structural formulas:

wherein each moiety D and each moiety A, independently, are selected from the group consisting of:

with the understanding that when more than one A or more than one D are present, all As and, independently, all Ds are the same,
wherein:
the (*) represents the point of attachment of the moieties A and D in the structural formulas (I) through (X);
Q is N, P, or As,
X is O, S, Se, —C(CH 3 ) 2 , or —Si(CH 3 ) 2 ,
Y is O, S, or Se,
Z is S or Se,
wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl,—OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 ; and
wherein the molecule comprises at least one atom selected from Si, Se, Ge, Sn, P, or As.

2. The compound of claim 1 , wherein the compound is represented by any one of the following structural formulas:

3. The compound of claim 1 , wherein each moiety D and each moiety A, independently, are selected from the group consisting of:

wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl, —OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 .

4. The compound of claim 3 , wherein at least one of the moieties A or D is

wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl, —OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 .

5. The compound of claim 4 , wherein at least one of the moieties A or D is

wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl, —OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 .

6. The compound of claim 4 , wherein at least one of the moieties A or D is

wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl, —OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 .

7. The compound of claim 3 , wherein at least one of the moieties A or D is

wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl, —OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 .

8. The compound of claim 7 , wherein at least one of the moieties A or D is

9. The compound of claim 3 , wherein at least one of the moieties A or D is

wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with one or more substituents selected from C 1 -C 6 alkyl, —OCH 3 , —SCH 3 , —C(CH 3 ) 3 , —Si(CH 3 ) 3 , —Ge(CH 3 ) 3 , or —Sn(CH 3 ) 3 .

10. The compound of claim 1 , wherein Z is Se.

11. The compound of claim 1 , wherein Q is N or P.

12. The compound of claim 11 , wherein Q is N.

13. The compound of claim 1 , wherein X is O, —C(CH 3 ) 2 , or —Si(CH 3 ) 2 .

14. The compound of claim 13 , wherein X is O or —C(CH 3 ) 2 .

15. The compound of claim 14 , wherein X is O.

16. The compound of claim 1 , wherein Y is O or Se.

17. The compound of claim 16 , wherein Y is Se.

18. The compound of claim 1 , wherein the compound comprises at least one atom selected from Si, Se, or P.

19. The compound of claim 1 , wherein the compound comprises at least one atom selected from Si or Se.

20. The compound of claim 1 , wherein the compound comprises Si.

21. The compound of claim 1 , wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with C 1 -C 6 alkyl, —OCH 3 , —C(CH 3 ) 3 , or —Si(CH 3 ) 3 .

22. The compound of claim 21 , wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with C 1 -C 6 alkyl or —Si(CH 3 ) 3 .

23. The compound of claim 22 , wherein the moiety A and the moiety D, for each occurrence independently, are optionally substituted with —Si(CH 3 ) 3 .

24. A molecule represented by a structural formula selected from the group consisting of:

25. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, and wherein the organic layer comprises at least one molecule of claim 1 .

Assignees

• Harvard College
• Massachusetts Inst Technology
• Presidents And Fellows Of Harvard College

Inventors

• Aspuru-Guzik Alan
• Gomez-Bombarelli Rafael
• Aguilera-Iparraguirre Jorge
• Baldo Marc
• Van Voorhis Troy
• Hirzel Timothy D
• Bahlke Matthias
• Mcmahon David
• Wu Tony Chang-Chi

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/5016

  Electricity · mapped topic

• C09K2211/1048

  with oxygen · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title