IP Library › Granted Patent US 12,284,915
Granted Patent B2
US 12,284,915 · App. 17/282,971 · Granted Apr 22, 2025

Organic electroluminescence device and electronic apparatus provided with the same

Inventors: Yuki Nakano (Sodegaura, JP); Taro Yamaki (Sodegaura, JP); Satomi Tasaki (Sodegaura, JP); Tomoki Kato (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H10K85/6574C07D307/91C07D487/22C07D493/04C07D493/10C07F5/027C09K11/06H10K85/30H10K85/615H10K85/626H10K85/633H10K85/636H10K85/6572C07B2200/05C09K2211/1018H10K50/11H10K50/15H10K50/16H10K85/622H10K85/624H10K2101/10
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Quick Facts
Patent No.
US 12,284,915
App. No.
17/282,971
Granted
Apr 22, 2025
Kind
B2
Abstract

An organic electroluminescence device including a cathode, an anode, and an emitting layer disposed between the cathode and the anode, wherein the emitting layer includes a compound represented by the following formula (1) and one or more compounds selected from the group consisting of compounds represented by each of formulas (11), (21), (31), (41), (51), (61), (71) and (81). In the formula (1), at least one of R 1 to R 8 is a deuterium atom.

Claims (386)

1. An organic electroluminescence device comprising:

a cathode,

an anode, and

an emitting layer disposed between the cathode and the anode, wherein

the emitting layer comprises a compound represented by the following formula (1) and one or more compounds selected from the group consisting of compounds represented by each of formulas (11), (21), (31), (41), (51), (61), (71) and (81):

wherein in the formula (1),

R 1 to R 8 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

when two or more of R 901 to R 907 exist, two or more of R 901 to R 907 may be the same with or different from each other;

at least one of R 1 to R 8 is a deuterium atom;

two or more adjacent groups of R 1 to R 4 and two or more adjacent groups of R 5 to R 8 do not form a ring;

L 1 and L 2 are independently

a single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

Ar is

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

one of R 11 to R 18 is a single bond bonding to L 2 ;

R 11 to R 18 which are not single bonds bonding to L 2 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in R 1 to R 8 ; and

two or more adjacent groups of R 11 to R 18 do not form a ring;

wherein, in the formula (11),

one or more pairs of two or more adjacent groups of R 101 to R 110 are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

at least one of R 101 to R 110 is a monovalent group represented by the formula (12);

R 101 to R 110 that do not form the substituted or unsubstituted, saturated or unsaturated ring and that are not a monovalent group represented by the following formula (12) are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

wherein, in the formula (12), Ar 101 and Ar 102 are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L 101 to L 103 are independently

a single bonded,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

wherein, in the formula (21),

Z's are independently CR a or N;

A1 ring and A2 ring are independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

when a plurality of R a s exist, one or more pairs of two or more adjacent groups of R a are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

when a plurality of R b s exist, one or more pairs of two or more adjacent groups of R b are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

when a plurality of R c s exist, one or more pairs of two or more adjacent groups of R c are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

n21 and n22 are independently an integer of 0 to 4;

R a to R c that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

wherein, in the formula (31),

one or more pairs of two or more adjacent groups of R 301 to R 307 and R 311 to R 317 form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring;

R 301 to R 307 and R 311 to R 317 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 321 and R 322 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

wherein, in the formula (41),

a ring, b ring and c ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

at least one of the ring b or ring c is a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms;

R 401 and R 402 are independently bonded to the a ring, the b ring or the c ring to form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring;

R 401 and R 402 that do not form the substituted or unsubstituted heterocyclic ring are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; and

at least one of the hydrogen atoms in formula (41) is a deuterium atom:

wherein, in the formula (51),

r ring is a ring represented by the formula (52) or formula (53) which is fused to an adjacent ring at an arbitrary position;

q ring and s ring are independently a ring represented by the formula (54) which is fused to an adjacent ring at an arbitrary position;

p ring and t ring are independently a ring represented by the formula (55) or the formula (56) which is fused to an adjacent ring at an arbitrary position;

when a plurality of R 501 s exist, adjacent R 501 s are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

X 501 is an oxygen atom, a sulfur atom, or NR 502 ;

R 501 and R 502 that do not form the substituted or unsubstituted saturated or unsaturated ring are

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

Ar 501 and Ar 502 are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L 501 is

a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3s are independently an integer of 0 to 3, and m4s are independently an integer of 0 to 5; when a plurality of R 501 s exist, R 501 s may be the same or different;

wherein, in the formula (61),

at least one pair of R 601 and R 602 , R 602 and R 603 , and R 603 and R 604 are bonded with each other to form a divalent group represented by the formula (62);

at least one pair of R 605 and R 606 , R 606 and R 607 , and R 607 and R 608 are bonded with each other to form a divalent group represented by formula (63);

at least one of R 601 to R 604 that does not form the divalent group represented by the formula (62), and R 611 to R 614 is a monovalent group represented by the following formula (64);

at least one of R 605 to R 608 that do not form the divalent group represented by the formula (63), and R 621 to R 624 is a monovalent group represented by the following formula (64);

X 601 is an oxygen atom, a sulfur atom, or NR 609 ;

R 601 to R 608 that do not form the divalent group represented by the formulas (62) and (63) and that is not the monovalent group represented by the formula (64), R 611 to R 614 and R 621 to R 624 that are not the monovalent group represented by the formula (64), and R 609 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

wherein, in the formula (64), Ar 601 and Ar 602 are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L 601 to L 603 are independently

a single bonded,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

a divalent linking group formed by bonding 2 to 4 above mentioned groups;

wherein, in the formula (71),

A 701 ring and A 702 ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

One or more rings selected from the group consisting of A 701 ring and A 702 ring are bonded to the bond * of the structure represented by the following formula (72);

wherein, in the formula (72),

A 703 rings are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

X 701 is NR 703 , C(R 704 )(R 705 ), Si(R 706 )(R 707 ), Ge(R 708 )(R 709 ), O, S or Se;

R 701 and R 702 are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form a substituted or unsubstituted saturated or unsaturated ring;

R 701 and R 702 that do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 703 to R 709 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

wherein, in the formula (81),

A 801 ring is a ring represented by the formula (82) which is fused to an adjacent ring at an arbitrary position;

A 802 ring is a ring represented by the formula (83) which is fused to an adjacent ring at an arbitrary position;

two bonds * bond to A 803 ring at an arbitrary position;

X 801 and X 802 are independently C(R 803 )(R 804 ), Si(R 805 )(R 806 ), an oxygen atom, or a sulfur atom;

A 803 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 801 to R 806 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

m801 and m802 are independently an integer of 0 to 2; when these are 2, a plurality of R 801 s or R 802 s may be the same or different;

a801 is an integer of 0 to 2; when a801 is 0 or 1, the structure in the parentheses indicated by “3-a801” may be the same as or different from each other; when a801 is 2, Ar 801 s may be the same or different from each other.

2. The organic electroluminescence device according to claim 1 , wherein in the formula (1), at least two of R 1 to R 8 are deuterium atoms.

3. The organic electroluminescence device according to claim 1 , wherein in the formula (1), R 1 to R 8 are all deuterium atoms.

4. The organic electroluminescence device according to claim 1 , wherein in the formula (1), one or more of L 1 and L 2 are a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms in which at least one of hydrogen atoms is a deuterium atom, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms in which at least one of hydrogen atoms is a deuterium atom.

5. The organic electroluminescence device according to claim 1 , wherein in the formula (1), wherein L1 and L2 are independently a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms.

6. The organic electroluminescence device according to claim 1 , wherein Ar is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one of hydrogen atoms is a deuterium atom, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms in which at least one of hydrogen atoms is a deuterium atom.

7. The organic electroluminescence device according to claim 1 , wherein in the formula (1), Ar is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

8. The organic electroluminescence device according to claim 7 , wherein in the formula (1), Ar is selected from groups represented by any of the following formulas (a1) to (a4):

wherein in the formulas (a1) to (a4), “*” is a single bond which bonds to L 1 ;

R 21 is

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1);

m1 is an integer of 0 to 4;

m2 is an integer of 0 to 5;

m3 is an integer of 0 to 7;

when each of m1 to m3 is two or more, a plurality of R 21 's are the same as or different from each other; and

when each of m1 to m3 is 2 or more, adjacent R 21 's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring.

9. The organic electroluminescence device according to claim 1 , wherein in the formula (1), R 11 to R 18 which are not a single bond bonded with L 2 are hydrogen atoms.

10. The organic electroluminescence device according to claim 1 , wherein in the formula (1), R 11 to R 18 which are not a single bond bonded with L 2 are deuterium atoms.

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

wherein in the formula (2), R 1 to R 8 , Ar, L 1 and L 2 are as defined in the formula (1).

12. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (3):

wherein in the formula (3), Ar, L 1 and L 2 are as defined in the formula (1).

13. The organic electroluminescence device according to claim 1 , wherein relative to the total amount of the compound represented by formula (1) and a compound having a structure same as the compound represented by the formula (1) and containing only protium atoms as hydrogen atoms, in the emitting layer, the content ratio of the latter is 99 mol % or less.

14. The organic electroluminescence device according to claim 1 , wherein in the formula (11), two of R 101 to R 110 are a group represented by the formula (12).

15. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (11) is a compound represented by the following formula (13):

wherein in the formula (13), R 111 to R 118 in the formula (11) are the same as R 101 to R 110 that are not a monovalent group represented by the formula (12); and Ar 101 , Ar 102 , L 101 , L 102 and L 103 are as defined in the formula (12).

16. The organic electroluminescence device according to claim 15 , wherein the compound represented by the formula (13) is a compound represented by the following formula (14):

wherein in the formula (14), R 111 to R 118 are as defined in the formula (13); and Ar 101 , Ar 102 , L 102 and L 103 are as defined in the formula (12).

17. The organic electroluminescence device according to claim 15 , wherein the compound represented by the formula (13) is a compound represented by the formula (15):

wherein in the formula (15), R 111 to R 118 are as defined in the formula (13); and Ar 101 and Ar 102 are as defined in the formula (12).

18. The organic electroluminescence device according to claim 15 , wherein the compound represented by the formula (13) is a compound represented by the formula (17):

wherein in the formula (17), R 111 to R 118 are as defined in the formula (13);

one ore more pairs of adjacent two or more of R 121 to R 127 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R 121 to R 127 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1); and

R 131 to R 135 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R 901 to R 907 are as defined in the formula (1).

19. The organic electroluminescence device according to claim 1 , wherein in the formula (41), R 401 and R 402 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

20. The organic electroluminescence device according to claim 1 , wherein in the formula (41), R 401 and R 402 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

21. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (41) is a compound represented by the following formula (42):

wherein in the formula (42),

R 401A forms a substituted or unsubstituted heterocyclic ring by bonding with one or more selected from the group consisting of R 411 and R 421 , or does not form a substituted or unsubstituted heterocyclic ring;

R 402A forms a substituted or unsubstituted heterocyclic ring by bonding with one or more selected from the group consisting of R 413 and R 414 , or does not form a substituted or unsubstituted heterocyclic ring;

R 401A and R 402A that do not form the substituted or unsubstituted heterocyclic ring are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

one or more pairs of adjacent two or more of R 411 to R 421 form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R 411 to R 421 that do not form the substituted or unsubstituted heterocyclic ring and the substituted or unsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; and

R 901 to R 907 are as defined in the formula (1).

22. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (41) is a compound represented by the following formula (43):

wherein in the formula (43)

R 431 forms a substituted or unsubstituted heterocyclic ring by bonding with R 446 , or does not form a substituted or unsubstituted heterocyclic ring;

R 433 forms a substituted or unsubstituted heterocyclic ring by bonding with R 447 , or does not form a substituted or unsubstituted heterocyclic ring;

R 434 forms a substituted or unsubstituted heterocyclic ring by bonding with R 451 , or does not form a substituted or unsubstituted heterocyclic ring;

R 441 forms a substituted or unsubstituted heterocyclic ring by bonding with R 442 , or does not form a substituted or unsubstituted heterocyclic ring;

one or more pairs of adjacent two or more of R 431 to R 451 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R 431 to R 451 that do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O—(R 904 ),

—S—(R 905 ),

—N(R 906 )(R 907 ),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; and

R 901 to R 907 are as defined in the formula (1).

23. The organic electroluminescence device according to claim 1 , which further comprises a hole-transporting layer between the anode and the emitting layer.

24. The organic electroluminescence device according to claim 1 , which further comprises an electron-transporting layer between the cathode and the emitting layer.

25. An electronic apparatus wherein the organic electroluminescence device according to claim 1 is provided.

26. The organic electroluminescence device according to claim 1 , wherein at least one of the ring b or ring c is a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms, said heterocyclic ring contains O or S.

27. The organic electroluminescence device according to claim 1 , wherein at least one of the ring b or ring c is a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms, wherein a substituent in said substituted or unsubstituted heterocyclic ring are 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,

a monovalent heterocyclic group including 5 to 50 ring atoms, and

Si(R 901 )(R 902 )(R 903 ).

28. The organic electroluminescence device according to claim 26 , wherein a substituent in said substituted or unsubstituted heterocyclic ring are 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,

a monovalent heterocyclic group including 5 to 50 ring atoms, and

Si(R 901 )(R 902 )(R 903 ).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2021
From: NAKANO, YUKI; YAMAKI, TARO; TASAKI, SATOMI; KATO, TOMOKI
To: IDEMITSU KOSAN CO.,LTD.
Reel/Frame 056727/0063 →
Priority Claims (4)
JP 2018-190838 · Oct 9, 2018 · national
JP 2018-191224 · Oct 9, 2018 · national
JP 2019-101578 · May 30, 2019 · national
JP 2019-101675 · May 30, 2019 · national
Continuity (3)
Continuation In Part 16557675 · Aug 30, 2019
Continuation In Part 16593743 · Oct 4, 2019
Related Publication 20230011996A1 · Jan 12, 2023
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