Organic electroluminescent device, compound and use thereof

1. An organic electroluminescent device containing an anode, a cathode and an organic layer formed between the anode and the cathode, wherein the organic layer contains a light-emitting layer containing a compound represented by the following formula (1):

wherein R 1 to R 6 each independently represent a hydrogen atom or a substituent; R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , and R 6 and R 7 may be taken together to form a ring; and R 7 represents a group represented by the following formula (2) or formula (3):

wherein Ar 11 represents an aryl group or an aryl-substituted aryl group; R 11 represents a substituent other than an aryl group; n11 represents an integer of from 1 to the number of substitutable positions in Ar 11 ; when n11 is 2 or more, then each R 11 may be the same or different; and at least one R 11 is an electron-donating group;

wherein R 21 to R 25 each independently represent a hydrogen atom or a substituent; and p is an integer of from 0 to 2; and

wherein the organic electroluminescent device exhibits a maximum emission wavelength at a range of from 700 to 1500 nm.

2. The organic electroluminescent device according to claim 1 , wherein the compound is represented by the following formula (11):

wherein Ar 12 and Ar 13 each independently represent an aryl group or an aryl-substituted aryl group; R 2 to R 6 each independently represent a hydrogen atom or a substituent; R 12 and R 13 each independently represent a substituent; R 3 and R 4 , and R 4 and R 5 may be taken together to form a ring; R 2 may be bonded to Ar 12 to form a ring and R 6 may be bonded to Ar 13 to form a ring; n12 represents an integer of from 1 to the number of substitutable positions in Ar 12 ; when n12 is 2 or more, then each R 12 may be the same or different; at least one R 12 is an electron-donating group; n13 represents an integer of from 1 to the number of substitutable positions in Ar 13 ; when n13 is 2 or more, then each R 13 may be the same or different; and at least one R 13 is an electron-donating group.

3. The organic electroluminescent device according to claim 2 , wherein at least one R 12 and at least one R 13 are each independently a substituted or unsubstituted diarylamino group.

4. The organic electroluminescent device according to claim 2 , wherein Ar 12 and Ar 13 each independently have a benzene structure, a naphthalene structure, an anthrathene structure or a fluorene structure.

5. The organic electroluminescent device according to claim 1 , wherein the compound is represented by the following formula (12):

wherein Ar 14 to Ar 17 each independently represent a substituted or unsubstituted aryl group; R 2 to R 6 each independently represent a hydrogen atom or a substituent; R 14 and R 15 each independently represent a substituent other than a substituted or unsubstituted diarylamino group; R 14 and R 2 , R 3 and R 4 , R 4 and R 5 , and R 6 and R 15 may be taken together to form a ring; n14 and n16 each independently represent an integer of 0 or more; n15 and n17 each independently represent an integer of 1 or more; n14+n15 is an integer of from 1 to 5 and n16+n17 is an integer of from 1 to 5; when n14 is 2 or more, then each R′ may be the same or different; when n15 is 2 or more, then each Ar 14 may be the same or different and each Ar 15 may be the same or different; when n16 is 2 or more, then each R 15 may be the same or different; when n17 is 2 or more, then each Ar 16 may be the same or different and each Ar 17 may be the same or different.

6. The organic electroluminescent device according to claim 1 , wherein R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a halogen atom, or a group containing a boron difluoride diketonate ring.

7. The organic electroluminescent device according to claim 1 , wherein R 3 and R 4 , or R 4 and R 5 are taken together to form a ring.

8. The organic electroluminescent device according to

claim 1 , wherein the compound is represented by the following formula (21):

wherein R 2 to R 6 and R 2′ to R 6′ each independently represent a hydrogen atom or a substituent; R 31 and R 32 each independently represent one of the Group A below; R 31 and R 2 , R 3 and R 4 , R 4 and R 5 , R 32 and R 2′ , R 3′ and R 4′ , and R 4′ and R 5′ may be taken together to form a ring; R 6 may be bonded to A to form a ring and R 7 may be bonded to A to form a ring; A represents a linking group represented by the following formula (22) or (24):

wherein n is an integer of from 0 to 4; m is 0 or 1; A′ represents an alkoxy group having 1 to 12 carbon atoms; and B′ represents a group represented by the following formula (23):

wherein R 2″ to R 6″ each independently represent a hydrogen atom or a substituent; and R 33 represents one of the Group A below;

wherein R 21 to R 24 each independently represent a hydrogen atom or a substituent; and p is an integer of from 0 to 2;

wherein each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group; and nBu represents a normal butyl group.

9. An organic electroluminescent device containing an anode, a cathode and an organic layer formed between the anode and the cathode, wherein the organic layer contains a light-emitting layer containing a compound represented by the following formula (1):

wherein R 1 to R 6 each independently represent a hydrogen atom or a substituent; R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 and R 6 and R 7 may be taken together to form a ring; and R 7 represents a group represented by the following formula (2) or formula (3):

wherein Ar 11 represents an aryl group or an aryl-substituted aryl group; RH represents a substituent other than an aryl group; n11 represents an integer of from 1 to the number of substitutable positions in Ar 11 ; when n11 is 2 or more, then each RH may be the same or different; and at least one R 11 is an electron-donating group;

wherein R 21 to R 25 each independently represent a hydrogen atom or a substituent; and p is an integer of from 0 to 2; and

wherein the organic electroluminescent device emits delayed fluorescence.

10. A compound represented by the following formula (12):

wherein Ar 14 to Ar 17 each independently represent a substituted or unsubstituted aryl group; R 2 , R 3 , R 5 and R 6 each independently represent a hydrogen atom or a substituent; R 4 represents a substituent; R 14 and R 15 each independently represent a substituent; R 14 and R 2 , R 3 and R 4 , R 4 and R 5 , and R 6 and R 15 may be taken together to form a ring; n14 and n16 each independently represent an integer of 0 or more; n15 and n17 each independently represent an integer of 1 or more; provided that n14+n15 is an integer of from 1 to 5 and n16+n17 is an integer of from 1 to 5; when n14 is 2 or more, then each R 14 may be the same or different; when n15 is 2 or more, then each of the diarylamino group in the parentheses of n15 may be the same or different; when n16 is 2 or more, then each R 15 may be the same or different; when n17 is 2 or more, then each of the diarylamino group in the parentheses of n17 may be the same or different.

11. An organic semiconductor laser, having an optical resonator structure and comprising a compound represented by the following formula (1) as an emitter:

wherein R 1 to R 6 each independently represent a hydrogen atom or a substituent; R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 and R 6 and R 7 may be taken together to form a ring; and R 7 represents a group represented by the following formula (2) or formula (3):

wherein Ar 11 represents an aryl group or an aryl-substituted aryl group; R 11 represents a substituent other than an aryl group; n11 represents an integer of from 1 to the number of substitutable positions in Ar 11 ; when n11 is 2 or more, then each R 11 may be the same or different; and at least one RH is an electron-donating group;

wherein R 21 to R 25 each independently represent a hydrogen atom or a substituent; and p is an integer of from 0 to 2.

12. The organic semiconductor laser according to claim 11 , wherein the optical resonator structure is composed of a second-order Bragg scattering region surrounded by a first-order Bragg scattering region.