Organic electroluminescence element and compound used therein

Patent metadata

Field	Value
Publication number	US-9660198-B2
Application number	US-201214233029-A
Country	US
Kind code	B2
Filing date	Jul 13, 2012
Priority date	Jul 15, 2011
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

An organic electroluminescence element in which a compound represented by the general formula below is used in a light-emitting layer exhibits a high emission efficiency and is inexpensive to provide. At least one of R 1 to R 8 and R 17 represent an electron-donating group and the others represent a hydrogen atom; at least one of R 9 to R 16 represent an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof and the others represent a hydrogen atom; Z represents a single bond or >C═Y; Y represents O, S, C(CN) 2 or C(COOH) 2 ; provided that when Z is a single bond, then at least one of R 9 to R 16 is an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof.

First claim

The invention claimed is:

1. An organic electroluminescence element having an anode, a cathode, and at least one organic layer containing a light-emitting layer between the anode and the cathode, wherein the light-emitting layer contains a compound represented by the following general formula (1):

wherein, in the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 17 each independently represent a hydrogen atom or an electron-donating group, and at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 or R 17 is an electron-donating group; R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, or an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof; Z represents >C═Y, Y represents C(CN) 2 .

2. An organic electroluminescence element having an anode, a cathode, and at least one organic layer containing a light-emitting layer between the anode and the cathode, wherein the light-emitting layer contains a compound represented by the following general formula (1), which radiates delayed fluorescence:

wherein, in the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 17 each independently represent a hydrogen atom or an electron-donating group, and at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 or R 17 is an electron-donating group; R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, or an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof; Z represents >C═Y, and Y represents O or C(CN) 2 .

3. The organic electroluminescence element according to claim 2 , wherein Z in the general formula (1) is a carbonyl group.

4. The organic electroluminescence element according to claim 1 , wherein R 17 in the general formula (1) is an aryl group.

5. The organic electroluminescence element according to claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 in the general formula (1) is an aryl group substituted with an electron-donating group.

6. The organic electroluminescence element according to claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 in the general formula (1) has a structure represented by the following general formula (2):

wherein, in the general formula (2), R 21 , R 22 , R 23 , R 24 and R 25 each independently represent a hydrogen atom or an electron-donating group, and at least one of R 21 , R 22 , R 23 , R 24 or R 25 is an electron-donating group.

7. The organic electroluminescence element according to claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 in the general formula (1) has a structure represented by any of the following general formulae (3) to (5):

wherein, in the above formulae, R 31 and R 32 each independently represent a substituted or unsubstituted aryl group; and the aryl group represented by R 31 may bond to the aryl group represented by R 32 ; R 41 , R 42 and R 43 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 41 and R 42 may together form a cyclic structure, and R 42 and R 43 may together form a cyclic structure; R 51 , R 52 and R 53 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 51 and R 52 may together form a cyclic structure, and R 52 and R 53 may together form a cyclic structure.

8. The organic electroluminescence element according to claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 in the general formula (1) has any of the following structures:

9. The organic electroluminescence element according to claim 1 , wherein at least one of R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 is a cyano group or has a structure represented by any of the following general formulae (6) to (9):

wherein, in the above formulae, R 61 and R 62 each independently represent a substituted or unsubstituted aryl group; R 71 and R 72 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and R 71 and R 72 may together form a cyclic structure; R 81 , R 82 and R 83 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; R 81 and R 82 may together form a cyclic structure, and R 82 and R 83 may together form a cyclic structure; R 91 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and Z represents a linking group necessary for forming a heteroaromatic ring.

10. The organic electroluminescence element according to claim 1 , wherein at least one of R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 in the general formula (1) has any of the following structures:

11. An organic electroluminescence element, wherein a compound represented by the following general formula (1) is used as a dopant in a light-emitting layer

wherein, in the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 17 each independently represent a hydrogen atom or an electron-donating group, and at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 or R 17 is an electron-donating group; R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, or an electron-withdrawing group that does not have an unshared electron pair at the α-position thereof; Z represents >C═Y, and Y represents O or C(CN) 2 .

12. A compound represented by the following general formula (1′):

wherein, in the general formula (1′), R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , R 6′ , R 7′ , R 8′ , and R 17′ each independently represent a hydrogen atom or an electron-donating group, and at least one of R 1′ , R 2′ , R 3′ , R 4′ , R 5′ , R 6′ , R 7′ , R 8′ or R 17′ is an electron-donating group; R 9′ , R 10′ , R 11′ , R 12′ , R 13′ , R 14′ , R 15′ and R 16′ each independently represent a hydrogen atom or a cyano group; Z′ represents >C═Y, and Y represents O or C(CN) 2 .

13. The compound according to claim 12 , wherein Z′ in the general formula (1′) is a carbonyl group.

14. The compound according to claim 12 , wherein Z′ in the general formula (1′) is >C═C(CN) 2 .

15. The compound according to claim 12 , wherein R 17′ in the general formula (1′) is an aryl group.

16. The compound according to claim 12 , wherein at least one of R

Assignees

• Nakagawa Tetsuya
• Adachi Chihaya
• Nomura Hiroko
• Mehes Gabor
• NASU Keiro
• Kyulux Inc

Inventors

• Nakagawa Tetsuya
• Adachi Chihaya
• Nomura Hiroko
• Mehes Gabor
• NASU Keiro

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D219/02 Primary

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

• C09K2211/1011

  Condensed systems · CPC title