IP Library › Granted Patent US 11,569,449

Granted Patent B2

US 11,569,449 · App. 16/345,213 · Granted Jan 31, 2023

Organic electroluminescence device and novel compound

Inventors: Ryota Takahashi (Sodegaura, JP); Hidetsugu Ikeda (Sodegaura, JP); Keita Seda (Sodegaura, JP); Yuki Nakano (Sodegaura, JP)

Assignee: IDEMITSU KOSAN CO., LTD.

H01L51/0061 C07D487/22 C07D491/22 C09K11/06 H01L51/006 H01L51/0052 H01L51/0058 H01L51/0072 H01L51/0073 H01L51/0074 H01L51/5012 C09K2211/1007 C09K2211/1018 H01L51/001 H01L51/5016 H01L51/5056 H01L51/5072 H01L51/5088 H01L51/5092 H01L51/5206 H01L51/5221 H01L51/56 H01L2251/301 H01L2251/308 H01L2251/558

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Quick Facts

Patent No.: US 11,569,449
App. No.: 16/345,213
Granted: Jan 31, 2023
Kind: B2

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Abstract

An organic electroluminescence device comprising: a cathode, an anode, and at least one organic layer disposed between the cathode and the anode, wherein at least one layer of the at least one organic layer comprises a compound represented by the following formulas (1-1) and (1-3) or a compound represented by the following formulas (1-2) and (1-3).

Claims (246)

1. An organic electroluminescence device comprising:

a cathode,

an anode, and

at least one organic layer disposed between the cathode and the anode, wherein

at least one layer of the at least one organic layer comprises a compound represented by the following formulas (1-1) and (1-3), or a compound represented by the following formulas (1-2) and (1-3):

wherein in the formulas (1-1), (1-2) and (1-3),

ring A is a substituted or unsubstituted fused aryl ring including 10 to 50 ring carbon atoms, a substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms or a benzene ring represented by the following formula (2);

two atomic bondings * in the formula (1-1) are respectively bonded with a ring carbon atom of the fused aryl ring of the ring A, a ring atom of the fused heterocyclic ring of the ring A, or a ring carbon atom of the benzene ring represented by the formula (2) of the ring A;

three atomic bondings * in the formula (1-2) are respectively bonded with a ring carbon atom of the fused aryl ring of the ring A, a ring atom of the fused heterocyclic ring of the ring A, or a ring carbon atom of the benzene ring represented by the formula (2) of the ring A;

one or more pairs of adjacent two or more of R 1 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 16 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

R 31 to R 37 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different;

wherein in the formula (2), at one of the two ring carbon atoms indicated by *, the atomic bonding extending from the benzene ring B in the formula (1-1) or the formula (1-2) is bonded, and at the other of the two ring carbon atoms indicated by *, the atomic bonding extending from the benzene ring C in the formula (1-3) is bonded;

R 17 is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different;

n is an integer of 1 or 2, and when n is 2, two R 17 s may be the same or different; and

a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, a haloalkyl group including 1 to 50 carbon atoms, a alkenyl group including 2 to 50 carbon atoms, a alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 ring carbon atoms, a alkoxy group including 1 to 50 carbon atoms, a alkylthio group including 1 to 50 carbon atoms, a aryloxy group including 6 to 50 ring carbon atoms, a arylthio group including 6 to 50 ring carbon atoms, a aralkyl group including 7 to 50 carbon atoms, —Si(R 41 )(R 42 )(R 43 ), —C(═O)R 44 , —COOR 45 , —S(═O) 2 R 46 , —P(═O)(R 47 )(R 48 ), —Ge(R 49 )(R 50 )(R 51 ), —N(R 52 )(R 53 ), a hydroxyl group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a monovalent heterocyclic group including 5 to 50 ring atoms;

R 41 to R 53 are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms or a monovalent heterocyclic group including 5 to 50 ring atoms;

when each of R 41 s to R 53 s are present in plural, each of the plural R 41 s to R 53 s may be the same or different; and

one or more pairs of adjacent two or more of the substituent in the “substituted or unsubstituted” do not form a substituted or unsubstituted, saturated or unsaturated ring.

2. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formulas (1-1) and (1-3), or a compound represented by the formulas (1-2) and (1-3) is the compound represented by the following formula (3), (4) or (5):

wherein in the formulas (3), (4) and (5),

the ring A′ is a substituted or unsubstituted fused aryl ring including 10 to 50 ring carbon atoms or a substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms, and

R 1 to R 7 and R 10 to R 17 are as defined in the formulas (1-1), (1-2), (1-3) and (2).

3. The organic electroluminescence device according to claim 1 , wherein the substituted or unsubstituted fused aryl ring including 10 to 50 ring carbon atoms is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring or a substituted or unsubstituted fluorene ring, and the substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring or a substituted or unsubstituted dibenzothiophene ring.

4. The organic electroluminescence device according to claim 1 , wherein the substituted or unsubstituted fused aryl ring including 10 to 50 ring carbon atoms is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring, and the substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring or a substituted or unsubstituted dibenzothiophene ring.

5. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formulas (1-1) and (1-3), or the compound represented by the formulas (1-2) and (1-3) is selected from the group consisting of compounds represented by the following formulas (6-1) to (6-6):

wherein in the formulas (6-1) to (6-6),

R 1 to R 17 are as defined in the formulas (1-1), (1-2), (1-3) and (2);

X is O, NR 25 or C(R 26 )(R 27 );

one or more pairs of adjacent two or more of R 21 to R 27 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 21 to R 27 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

when each of R 31 to R 37 is present in plural, each of the plural R 31 to R 37 may be the same or different.

6. The organic electroluminescence device according to claim 1 , wherein R 1 to R 17 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

7. The organic electroluminescence device according to claim 1 , wherein R 1 to R 17 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 18 ring atoms.

8. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formulas (1-1) and (1-3), or the compound represented by the formulas (1-2) and (1-3) is the compound represented by the following formula (3-2):

wherein in the formula (3-2),

R 3 , R 5 , R 6 , R 10 , R 12 and R 13 are as defined in the formulas (1-1) and (1-3).

9. The organic electroluminescence device according to claim 1 , wherein a substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a monovalent heterocyclic group including 5 to 50 ring atoms.

10. The organic electroluminescence device according to claim 1 , wherein a substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, or a monovalent heterocyclic group including 5 to 18 ring atoms.

11. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formulas (1-1) and (1-3) or the compound represented by the formulas (1-2) and (1-3) is the compound represented by the following formula (3-11):

wherein in the formula (3-11),

one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 7 and R 10 to R 16 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, provided that at least one of R 1 to R 7 and R 10 to R 16 is —N(R 36 )(R 37 );

two R 17 s may be the same or different;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different.

12. The organic electroluminescence device according to claim 11 , wherein the compound represented by the formula (3-11) is the compound represented by the following formula (3-12):

wherein in the formula (3-12),

one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 7 and R 10 to R 16 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, provided that any two of R 1 to R 7 and R 10 to R 16 is —N(R 36 )(R 37 );

two R 17 s may be the same or different;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different.

13. The organic electroluminescence device according to claim 11 , wherein the compound represented by the formula (3-11) is the compound represented by the following formula (3-13):

wherein in the formula (3-13),

one or more pairs of adjacent two or more of R 1 to R 4 and R 10 to R 13 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 4 , R 10 to R 13 and R 17 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 18 ring atoms;

two R 17 s may be the same or different; and

R A , R B , R C and R D are independently a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 18 ring atoms.

14. The organic electroluminescence device according to claim 13 , wherein the compound represented by the formula (3-13) is the compound represented by the formula (3-14):

wherein in the formula (3-14), R 17 , R A , R B , R C and R D are as defined in the formula (3-13).

15. The organic electroluminescence device according to claim 13 , wherein R A , R B , R C and R D are independently a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms.

16. The organic electroluminescence device according to claim 13 , wherein R A , R B , R C and R D are independently a substituted or unsubstituted phenyl group.

17. The organic electroluminescence device according to claim 11 , wherein two R 17 s are hydrogen atoms.

18. The organic electroluminescence device according to claim 11 , wherein a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, and a monovalent heterocyclic group including 5 to 18 ring atoms.

19. The organic electroluminescence device according to claim 11 , wherein a substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 5 carbon atoms.

20. The organic electroluminescence device according to claim 1 , wherein the at least one layer of the at least one organic layer is an emitting layer.

21. The organic electroluminescence device according to claim 20 , wherein the emitting layer further comprises a compound represented by the following formula (10):

wherein in the formula (10),

one or more pairs of two or more adjacent R 101 to R 110 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 101 to R 110 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 121 )(R 122 )(R 123 ), —C(═O)R 124 , —COOR 125 , —N(R 126 )(R 127 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, or a group represented by the following formula (31);

R 121 to R 127 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when each of R 121 to R 127 is present in plural, each of the plural R 121 to R 127 may be the same or different;

provided that at least one of R 101 to R 110 that do not form the substituted or unsubstituted, saturated or unsaturated ring is a group represented by the following formula (31); when two or more groups represented by the formula (31) are present, each of these groups may be the same or different;

-L 101 -Ar 101 (31)

wherein in the formula (31),

L 101 is a single bond, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms;

Ar 101 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.

22. The organic electroluminescence device according to claim 21 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-1) or (10-2):

wherein in the formula (10-1), R 101 to R 108 , L 101 and Ar 101 are as defined in the formula (10);

wherein in the formula (10-2), R 101 , R 103 to R 108 , L 101 and Ar 101 are as defined in the formula (10).

23. The organic electroluminescence device according to claim 21 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-3):

wherein in the formula (10-3),

R 101A to R 108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;

L 101A is a single bond or a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, and the two L 101A s may be the same or different;

Ar 101A is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and the two Ar 101A s may be the same or different.

24. The organic electroluminescence device according to claim 21 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-4):

wherein in the formula (10-4),

L 101 and Ar 101 are as defined in the formula (10);

R 101A to R 108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;

X 11 is O, S, or N(R 61 );

R 61 is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;

one of R 62 to R 69 is an atomic bonding that is bonded with L 101 ;

one or more pairs of two or more adjacent R 62 to R 69 that are not bonded with L 101 may be bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring; and

R 62 to R 69 that are not bonded with L 101 and do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.

25. The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-6):

wherein in the formula (10-6),

L 101 and Ar 101 are as defined in the formula (10);

R 101A to R 108A are as defined in the formula (10-4);

R 66 to R 69 are as defined in the formula (10-4); and

X 12 is O or S.

26. The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-7):

wherein in the formula (10-7),

L 101 and Ar 101 are as defined in the formula (10);

R 101A to R 108A are as defined in the formula (10-4);

X 11 is as defined in the formula (10-4); and

R 62 to R 69 are as defined in the formula (10-4), provided that any one pair of R 66 and R 67 , R 67 and R 68 , and R 68 and R 69 are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring.

27. The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-8):

wherein in the formula (10-8),

L 101 and Ar 101 are as defined in the formula (10);

R 101A to R 108A are as defined in the formula (10-4);

X 12 is O or S; and

R 66 to R 69 are as defined in the formula (10-4), provided that any one pair of R 66 and R 67 , R 67 and R 68 , as well as R 68 and R 69 are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring.

28. The organic electroluminescence device according to claim 26 , wherein any one pair of R 66 and R 67 , R 67 and R 68 , as well as R 68 and R 69 are bonded with each other to form a ring represented by the following formula (10-8-1) or (10-8-2), and

R 66 to R 69 that do not form the ring represented by the formula (10-8-1) or (10-8-2) do not form a substituted or unsubstituted, saturated or unsaturated ring,

wherein in the formulas (10-8-1) and (10-8-2),

the two atomic bondings * are independently bonded with one pair of R 66 and R 67 , R 67 and R 68 , or R 68 and R 69 ;

R 80 to R 83 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; and

X 13 is O or S.

29. The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-9):

wherein in the formula (10-9),

L 101 and Ar 101 are as defined in the formula (10);

R 101A to R 108A are as defined in the formula (10-4);

R 66 to R 69 are as defined in the formula (10-4), provided that R 66 and R 67 , R 67 and R 68 , as well as R 69 and R 67 are not bonded with each other and do not form a substituted or unsubstituted, saturated or unsaturated ring; and

X 12 is O or S.

30. The organic electroluminescence device according to claim 21 , wherein the compound represented by the formula (10) is the compound represented by the following formula (10-4A):

wherein in the formula (10-4A),

L 101 and Ar 101 are as defined in the formula (10);

R 101A to R 108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;

X 11 is O, S or N(R 61 );

R 61 is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;

one or more pairs of adjacent two or more of R 62A to R 69A may form a substituted or unsubstituted, saturated or unsaturated ring, and adjacent two of R 62A to R 69A form a ring represented by the following formula (10-4A-1); and

R 62A to R 69A that do not form a substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;

wherein in the formula (10-4A-1),

each of the two atomic bondings * is bonded with adjacent two of R 62A to R 69A ;

one of R 70 to R 73 is an atomic bonding that is bonded with L 101 ; and

R 70 to R 73 that are not bonded with L 101 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.

31. The organic electroluminescence device according to claim 20 , which has a hole-transporting layer between the anode and the emitting layer.

32. The organic electroluminescence device according to claim 20 , which has an electron-transporting layer between the cathode and the emitting layer.

33. An electronic apparatus provided with the organic electroluminescence device according to claim 1 .

34. A compound represented by the following formula (3), (4) or (5):

wherein in the formulas (3), (4) and (5),

the ring A′ is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms;

one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 17 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 7 and R 10 to R 17 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

when each of R 31 to R 37 is present in plural, each of the plural R 31 to R 37 may be the same or different in the formulas (3) and (4), at least one of R 1 to R 7 and R 10 to R 17 is a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —N(R 36 )(R 37 ), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; or at least one pair of adjacent two or more of R 1 to R 16 forms a substituted or unsubstituted, saturated or unsaturated ring;

when each of R 41 s to R 53 s are present in plural, each of the plural R 41 s to R 53 s may be the same or different; and

one or more pairs of adjacent two or more of the substituent in the “substituted or unsubstituted” do not form a substituted or unsubstituted, saturated or unsaturated ring.

35. The compound according to claim 34 , wherein the substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring or a substituted or unsubstituted dibenzothiophene ring.

36. The compound according to claim 34 , wherein R 1 to R 7 and R 10 to R 17 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

37. The compound according to claim 34 , wherein R 1 to R 7 and R 10 to R 17 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 18 ring atoms.

38. The compound according to claim 34 , which is represented by the following formula (3-2):

wherein in the formula (3-2), R 3 , R 5 , R 6 , R 10 , R 12 and R 13 are as defined in the formulas (3), (4) and (5).

39. The compound according to claim 34 , wherein a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, and a monovalent heterocyclic group including 5 to 50 ring atoms.

40. The compound according to claim 34 , wherein a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, and a monovalent heterocyclic group including 5 to 18 ring atoms.

41. A compound represented by the following formula (3-11):

wherein in the formula (3-11),

one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

two R 17 s may be the same or different;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different;

when each of R 41 s to R 53 s are present in plural, each of the plural R 41 s to R 53 s may be the same or different; and

one or more pairs of adjacent two or more of the substituent in the “substituted or unsubstituted” do not form a substituted or unsubstituted, saturated or unsaturated ring.

42. The compound according to claim 41 , which is represented by the following formula (3-12):

wherein in the formula (3-12),

one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 7 and R 10 to R 16 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, provided that any two of R 1 to R 7 and R 10 to R 16 is —N(R 36 )(R 37 );

two R 17 s may be the same or different;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different.

43. The compound according to claim 41 , which is represented by the following formula (3-13):

wherein in the formula (3-13),

one or more pairs of adjacent two or more of R 1 to R 4 and R 10 to R 13 may form a substituted or unsubstituted, saturated or unsaturated ring;

two R 17 s may be the same or different; and

44. The compound according to claim 43 , which is represented by the formula (3-14):

wherein in the formula (3-14), R 17 , R A , R B , R C and R D are as defined in the formula (3-13).

45. The compound according to claim 43 , wherein R A , R B , R C and R D are independently a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms.

46. The compound according to claim 43 , wherein R A , R B , R C and R D are independently a substituted or unsubstituted phenyl group.

47. The compound according to claim 41 , wherein two R 17 s are hydrogen atoms.

48. The compound according to claim 41 , wherein a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, and a monovalent heterocyclic group including 5 to 18 ring atoms.

49. The compound according to claim 41 , wherein a substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 5 carbon atoms.

50. The compound according to claim 41 , which is represented by the formula (3-21):

wherein in the formula (3-21),

one or more pairs of adjacent two or more of R 1 to R 4 and R 10 to R 13 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 1 to R 4 and R 10 to R 13 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 20 ring atoms;

and

R A , R B , R C and R D are independently a substituted or unsubstituted phenyl group; and two R 17 s are hydrogen atoms.

51. The compound according to claim 50 , wherein

a substituent in the “substituted or unsubstituted” is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, and a monovalent heterocyclic group including 5 to 20 ring atoms.

52. The compound according to claim 50 , wherein

a substituent in the “substituted or unsubstituted” is an alkyl group including 1 to 5 carbon atoms.

53. A material for an organic electroluminescence device comprising the compound according to claim 34 .

54. A material for an organic electroluminescence device comprising the compound according to claim 41 .

55. A compound represented by the following formulas (1-2) and (1-3):

wherein in the formulas (1-2) and (1-3),

one or more pairs of adjacent two or more of R 2 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 2 to R 16 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different; and

when the ring A is a benzene ring represented by the formula (2), at least one of R 2 to R 17 is a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —N(R 36 )(R 37 ), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; or at least one pair of adjacent two or more of R 2 to R 16 forms a substituted or unsubstituted, saturated or unsaturated ring;

wherein in the formula (2), at one of the two ring carbon atoms indicated by *, the atomic bonding extending from the benzene ring B in the formula (1-2) is bonded, and at the other of the two ring carbon atoms indicated by *, the atomic bonding extending from the benzene ring C in the formula (1-3) is bonded;

when each of R 31 to R 37 is present in plural, each of the plural R 31 s to R 37 s may be the same or different;

n is an integer of 1 or 2, and when n is 2, two R 17 s may be the same or different;

when each of R 4i s to R 53 s are present in plural, each of the plural R 41 s to R 53 s may be the same or different; and

one or more pairs of adjacent two or more of the substituent in the “substituted or unsubstituted” do not form a substituted or unsubstituted, saturated or unsaturated ring.

56. The compound according to claim 55 , wherein R 2 to R 16 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 18 ring atoms.

57. A compound represented by the following formula (6-5), (6-6), (6-8), (6-9), or (6-10):

wherein in the formulas (6-5), (6-6), (6-8), (6-9), and (6-10),

one or more pairs of adjacent two or more of R 1 to R 7 and R 10 to R 16 may form a substituted or unsubstituted, saturated or unsaturated ring;

X is O, NR 25 or C(R 26 )(R 27 );

one or more pairs of adjacent two or more of R 21 to R 27 may form a substituted or unsubstituted, saturated or unsaturated ring;

when each of R 31 to R 37 is present in plural, each of the plural R 31 to R 37 may be the same or different;

when each of R 41 s to R 53 s are present in plural, each of the plural R 41 s to R 53 s may be the same or different; and

one or more pairs of adjacent two or more of the substituent in the “substituted or unsubstituted” do not form a substituted or unsubstituted, saturated or unsaturated ring.

58. The compound according to claim 57 , wherein R 1 to R 7 and R 10 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 18 ring atoms.

59. The compound according to claim 34 , which is represented by the following formulas (6-1) to (6-4):

wherein in the formulas (6-1) to (6-4), one or more pairs of adjacent two or more of R 21 to R 24 may form a substituted or unsubstituted, saturated or unsaturated ring;

R 21 to R 24 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, —Si(R 31 )(R 32 )(R 33 ), —C(═O)R 34 , —COOR 35 , —N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

when each of R 31 to R 37 is present in plural, each of the plural R 31 to R 37 may be the same or different.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2019

From: TAKAHASHI, RYOTA; IKEDA, HIDETSUGU; SEDA, KEITA; NAKANO, YUKI

To: IDEMITSU KOSAN CO., LTD.

Reel/Frame 049865/0628 →

Priority Claims (2)

JP JP2017-234331 · Dec 6, 2017 · national

JP JP2018-114580 · Jun 15, 2018 · national

Continuity (3)

Continuation 16201984 · Nov 27, 2018

Continuation 16043074 · Jul 23, 2018

Related Publication 20190341556A1 · Nov 7, 2019

Cited By (1)

US 12,550,610