Polycyclic aromatic compound and light emission layer-forming composition

1. A light emitting layer-forming composition for applying and forming a light emitting layer of an organic electroluminescent element, comprising:

at least one selected from the group consisting of a polycyclic aromatic compound represented by the following general formula (A) and a polycyclic aromatic multimer compound having a plurality of structures represented by the following general formula (A) as a first component;

at least one selected from the group consisting of compounds represented by the following general formulas (B-1) to (B-6) as a second component; and

at least one organic solvent as a third component

wherein in the above formula (A) ring A, ring B, and ring C each independently represent an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be substituted,

Y 1 represents B,

X 1 and X 2 each independently represent O or N—R, while at least one of X 1 and X 2 represents N—R, R of the N—R is an optionally substituted aryl, an optionally substituted heteroaryl or alkyl, R of the N—R may be bonded to the ring A, ring B, and/or ring C with a linking group or a single bond,

at least one hydrogen atom in a compound or a structure represented by the above formula (A) may be substituted by a group represented by the following general formula (FG-1), a group represented by the following general formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom, further any —CH 2 — in the alkyl may be substituted by —O— or —Si(CH 3 ) 2 —, any —CH 2 — excluding —CH 2 — directly bonded to the compound or structure represented by the above formula (A) in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom

wherein in the above formulas (B-1) to (B-4) Ar's each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino,

adjacent groups among Ar's may be bonded to each other to form an aryl ring or a heteroaryl ring together with a mother skeleton of an anthracene ring, a pyrene ring, a fluorene ring, or a carbazole ring, at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, and

n represents an integer of 1 to a maximum substitutable number;

wherein in the above formula (B-5) R 1 to R 11 each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino,

adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, and at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino;

wherein in the above formula (B-6) monomer units (MU's) each independently represent at least one selected from the group consisting of divalent groups of compounds represented by the above general formulas (B-1) to (B-5), two hydrogen atoms in MU are substituted by an endcap unit (EC) or MU,

EC's each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, at least one hydrogen in these may be further substituted by an aryl, a heteroaryl, or a diarylamino, and

k is an integer of 2 to 50,000;

at least one hydrogen atom in compounds represented by the above formulas (B-1) to (B-5), a divalent group of compounds represented by the above formulas (B-1) to (B-5) in the above formula (B-6), or EC in the above formula (B-6) may be substituted by a group represented by the following general formula (FG-1), a group represented by the following general formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom,

further any —CH 2 — in the alkyl may be substituted by —O— or —Si(CH 3 ) 2 —, any —CH 2 — in the alkyl excluding —CH 2 — directly bonded to compounds represented by the above formulas (B-1) to (B-6), a divalent group of a compound represented by the above formulas (B-1) to (B-5) in the above formula (B-6), or EC in the above formula (B-6) may be substituted by an arylene having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom;

wherein in the above formula (FG-1) R's each independently represent a fluorine atom, a trimethylsilyl, a trifluoromethyl, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, any —CH 2 — in the alkyl may be substituted by —O—, any —CH 2 -excluding —CH 2 — directly bonded to a phenyl or a phenylene in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, at least one hydrogen atom in the cycloalkyl may be substituted by an alkyl having 1 to 24 carbon atoms or an aryl having 6 to 12 carbon atoms,

when two adjacent R's each represent an alkyl or a cycloalkyl, these R's may be bonded to each other to form a ring,

m's each independently represent an integer of 0 to 4,

n represents an integer of 0 to 5, and

p represents an integer of 1 to 5;

wherein in the above formula (FG-2) R's each independently represent a fluorine atom, a trimethylsilyl, a trifluoromethyl, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or an aryl having 6 to 12 carbon atoms, any —CH 2 — in the alkyl may be substituted by —O—, any —CH 2 — excluding —CH 2 — directly bonded to a phenyl or a phenylene in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, at least one hydrogen atom in the cycloalkyl may be substituted by an alkyl having 1 to 24 carbon atoms or an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in the aryl may be substituted by an alkyl having 1 to 24 carbon atoms,

when two adjacent R's each represent an alkyl or a cycloalkyl, these R's may be bonded to each other to form a ring,

m represents an integer of 0 to 4, and

n's each independently represent an integer of 0 to 5.

2. The light emitting layer-forming composition described in claim 1 , in which the first component is at least one selected from the group consisting of a polycyclic aromatic compound represented by the following general formula (A′) and a polycyclic aromatic multimer compound having a plurality of structures represented by the following general formula (A′)

wherein in the above formula (A′) R 1 to R 11 each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, while at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino,

adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino,

Y 1 represents B,

X 1 and X 2 each independently represent O or N—R, while at least one of X 1 and X 2 represents N—R, R of the N—R is an aryl or an alkyl, R of the N—R may be bonded to ring b and/or ring c with —O—, —S—, —C(—R) 2 —, or a single bond, R in the —C(—R) 2 — represents an alkyl having 1 to 24 carbon atoms,

at least one hydrogen atom in a compound or a structure represented by the above formula (A′) may be substituted by a group represented by the above general formula (FG-1), a group represented by the above general formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom, further any —CH 2 — in the alkyl may be substituted by —O— or —Si(CH 3 ) 2 —, any —CH 2 — excluding —CH 2 — directly bonded to the compound or structure represented by the above formula (A′) in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom.

3. The light emitting layer-forming composition described in claim 2 , in which

R 1 to R 11 each independently represent a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b, or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

Y 1 represents B,

X 1 and X 2 each independently represent O or N—R, while at least one of X 1 and X 2 represents N—R, R of the N—R is an aryl having 6 to 18 carbon atoms or an alkyl having 1 to 12 carbon atoms,

at least one hydrogen atom in a compound or a structure represented by the above formula (A′) may be substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom.

4. The light emitting layer-forming composition described in claim 1 , in which the polycyclic aromatic multimer compound is a dimer compound or a trimer compound having two or three structures represented by the above formula (A) or the above formula (A′).

5. The light emitting layer-forming composition described in claim 4 , in which the polycyclic aromatic multimer compound is a dimer compound having two structures represented by the above formula (A) or the above formula (A′).

6. The light emitting layer-forming composition described in claim 1 , in which

in the above formulas (B-1) to (B-4),

Ar's each independently represent a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

adjacent groups among Ar's may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with a mother skeleton of an anthracene ring, a pyrene ring, a fluorene ring, or a carbazole ring, at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

n represents an integer of 1 to 8,

in the above formula (B-5),

R 1 to R 11 each independently represent a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino (the aryl is an aryl having 6 to 12 carbon atoms), at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b, or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

in the above formula (B-6),

MU's each independently represent at least one selected from the group consisting of divalent groups of compounds represented by the above general formulas (B-1) to (B-5), two hydrogen atoms in MU are substituted by EC or MU,

EC's each independently represent a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino, wherein the aryl is an aryl having 6 to 12 carbon atoms,

k is an integer of 100 to 40000,

at least one hydrogen atom in the compounds represented by the above formulas (B-1) to (B-5), a divalent group of compounds represented by the above formulas (B-1) to (B-5) in the above formula (B-6), or EC in the above formula (B-6) may be substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom.

7. The light emitting layer-forming composition described in claim 1 , in which at least one compound in the first component or the second component is substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms.

8. The light emitting layer-forming composition described in claim 1 , in which at least one compound in the second component is substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms.

9. The light emitting layer-forming composition described in claim 1 , in which the second component comprises at least one selected from the group consisting of compounds represented by the above formulas (B-1) to (B-5).

10. The light emitting layer-forming composition described in claim 1 , in which the second component comprises at least one selected from the group consisting of a compound represented by the above formula (B-1) and a compound represented by the above formula (B-5).

11. The light emitting layer-forming composition described in claim 1 , in which the second component comprises a compound represented by the above formula (B-5).

12. The light emitting layer-forming composition described in claim 1 , in which

Ar's in the above formulas (B-1) to (B-4), R 1 to R 11 in the above formula (B-5), and EC in the above formula (B-6) each independently represent any one selected from the group consisting of a hydrogen atom and groups represented by the following formulas (RG-1) to (RG-10), and

each of groups represented by the following formulas (RG-1) to (RG-10) is bonded to the above formulas (B-1) to (B-6) at *

13. The light emitting layer-forming composition described in claim 1 , in which

a compound represented by the above formula (B-5) is a compound represented by the following formula (B-5-1-z), (B-5-49-z), (B-5-91-z), (B-5-100-z), (B-5-152-z), (B-5-176-z), (B-5-1048-z), (B-5-1049-z), (B-5-1050-z), (B-5-1069-z), (B-5-1101-z), (B-5-1102-z), or (B-5-1103-z)

wherein z's in the above formulas each represent a hydrogen atom, a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms, and not all z's represent hydrogen atoms.

14. The light emitting layer-forming composition described in claim 10 , in which the second component comprises a compound represented by the above formula (B-1).

15. The light emitting layer-forming composition described in claim 1 , in which the compound represented by the above formula (B-1) is a compound represented by the following general formula (B-11)

wherein in the above formula (B-11) X's each independently represent a group represented by the above formula (B-11-X1), (B-11-X2), or (B-11-X3), a naphthylene moiety in formula (B-11-X1) or (B-11-X2) may be fused with one benzene ring, a group represented by formula (B-11-X1), (B-11-X2), or (B-11-X3) is bonded to formula (B-11) at *, two X's do not simultaneously represent a group represented by formula (B-11-X3), Ar 1 , Ar 2 , and Ar 3 each independently represent a hydrogen atom (excluding Ar 3 ), a phenyl, a biphenylyl, a terphenylyl, a quaterphenylyl, a naphthyl, a phenanthryl, a fluorenyl, a benzofluorenyl, a chrysenyl, a triphenylenyl, a pyrenylyl, a carbazolyl, a benzocarbazolyl, or a phenyl-substituted carbazolyl, Ar 3 may be further substituted by a phenyl, a biphenylyl, a terphenylyl, a naphthyl, a phenanthryl, a fluorenyl, a chrysenyl, a triphenylenyl, a pyrenylyl, a carbazolyl, or a phenyl-substituted carbazolyl,

Ar 4 's each independently represent a hydrogen atom, a phenyl, a biphenylyl, a terphenylyl, a naphthyl, or a silyl substituted by an alkyl having 1 to 4 carbon atoms, and

at least one hydrogen atom in a compound represented by the above formula (B-11) may be substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms.

16. The light emitting layer-forming composition described in claim 15 , in which,

X's each independently represent a group represented by the above formula (B-11-X1), (B-11-X2), or (B-11-X3), the group represented by formula (B-11-X1), (B-11-X2), or (B-11-X3) is bonded to formula (B-11) at *, two X's do not simultaneously represent a group represented by formula (B-11-X3), Ar 1 , Ar 2 , and Ar 3 each independently represent a hydrogen atom (excluding Ar 3 ), a phenyl, a biphenylyl, a terphenylyl, a naphthyl, a phenanthryl, a fluorenyl, a chrysenyl, a triphenylenyl, a pyrenylyl, a carbazolyl, or a phenyl-substituted carbazolyl, Ar 3 may be further substituted by a phenyl, a biphenylyl, a terphenylyl, a naphthyl, a phenanthryl, a fluorenyl, a chrysenyl, a triphenylenyl, a pyrenylyl, a carbazolyl, or a phenyl-substituted carbazolyl,

Ar 4 's each independently represent a hydrogen atom, a phenyl, or a naphthyl, and

at least one hydrogen atom in a compound represented by the above formula (B-11) may be substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms.

17. The light emitting layer-forming composition described in claim 15 , in which,

X's each independently represent a group represented by the above formula (B-11-X1), (B-11-X2), or (B-11-X3), the group represented by formula (B-11-X1), (B-11-X2), or (B-11-X3) is bonded to formula (B-11) at *, two X's do not simultaneously represent a group represented by formula (B-11-X3), Ar 1 , Ar 2 , and Ar 3 each independently represent a hydrogen atom (excluding Ar 3 ), a phenyl, a biphenylyl, a terphenylyl, a naphthyl, a phenanthryl, a fluorenyl, a carbazolyl, or a phenyl-substituted carbazolyl, Ar 3 may be further substituted by a phenyl, a naphthyl, a phenanthryl, or a fluorenyl,

Ar 4 's each independently represent a hydrogen atom, a phenyl, or a naphthyl, and

at least one hydrogen atom in a compound represented by the above formula (B-11) may be substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms.

18. The light emitting layer-forming composition described in claim 1 , in which

the compound represented by the above formula (B-1) is a compound represented by the following formula (B-1-1), (B-1-2), (B-1-3), (B-1-4), (B-1-5), (B-1-6), (B-1-7), or (B-1-8), and

at least one hydrogen atom in these compounds may be substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms

19. The light emitting layer-forming composition described in claim 1 , in which at least one compound in the first component is substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms.

20. The light emitting layer-forming composition described in claim 1 , in which X 1 and X 2 each represent N—R.

21. The light emitting layer-forming composition described in claim 1 , in which X 1 represents O, and X 2 represents N—R.

22. The light emitting layer-forming composition described in claim 2 , in which

in the above formula (A′), R 1 to R 11 each independently represent any one selected from the group consisting of a hydrogen atom and groups represented by the following formulas (RG-1) to (RG-10), and

the groups represented by the following formulas (RG-1) to (RG-10) are each bonded to the above formula (A′) at *

23. The light emitting layer-forming composition described in claim 1 , in which

the compound represented by the above formula (A) is a compound represented by the following formula (1-401-z), (1-411-z), (1-422-z), (1-447-z), (1-1152-z), (1-1159-z), (1-1201-z), (1-1210-z), (1-2623-z), or (1-2679-z)

wherein z's in the above formulas each represent a hydrogen atom, a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms, and not all z's represent hydrogen atoms.

24. The light emitting layer-forming composition described in claim 23 , in which the compound represented by the above formula (A) is a compound represented by the above formula (1-422-z), (1-1152-z), or (1-2679-z).

25. The light emitting layer-forming composition described in claim 1 , in which

in the above formula (FG-1), m and n each represent 0, and p represents an integer of 1 to 3, and

in the formula (FG-2), m and n each represent 0.

26. The light emitting layer-forming composition described in claim 1 , in which at least one compound in the first component or the second component is substituted by a group represented by the above formula (FG-1).

27. The light emitting layer-forming composition described in claim 1 , in which the boiling point of at least one organic solvent in the third component is from 130° C. to 300° C.

28. The light emitting layer-forming composition described in claim 1 , in which

the third component comprises a good solvent (GS) and a poor solvent (PS) for at least one compound represented by the above formulas (B-1) to (B-6), and the boiling point (BP GS ) of the good solvent (GS) is lower than the boiling point (BP PS ) of the poor solvent (PS).

29. The light emitting layer-forming composition described in claim 1 , in which

the content of the first component is from 0.0001% by weight to 2.0% by weight with respect to the total weight of the light emitting layer-forming composition,

the content of the second component is from 0.0999% by weight to 8.0% by weight with respect to the total weight of the light emitting layer-forming composition, and

the content of the third component is from 90.0% by weight to 99.9% by weight with respect to the total weight of the light emitting layer-forming composition.

30. An organic electroluminescent element comprising a light emitting layer formed using the light emitting layer-forming composition described in claim 1 .

31. A display apparatus comprising the organic electroluminescent element described in claim 30 .