IP Library Granted Patent US 12709604
Granted Patent B2
US 12709604 · App. 17/906,953 · Granted Aug 18, 2026

Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device

Inventors: Tasuku Haketa (Sodegaura, JP); Yusuke Takahashi (Sodegaura, JP); Shota Tanaka (Sodegaura, JP); Hirokatsu Ito (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
C07D333/76C07D409/12H10K50/156H10K85/633H10K85/636H10K50/15H10K85/626H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12709604
App. No.
17/906,953
Granted
Aug 18, 2026
Kind
B2
Abstract

A compound may be capable of further improving the capability of an organic EL device. An organic electroluminescent device may have a further improved device capability using such compound(s). An electronic device may include such an organic electroluminescent device. Such compounds may have formula (1) wherein the symbols are as defined in the description.

Claims (78)

1 . A compound of formula if formula (1):

wherein

R 1 to R 8 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

provided that one selected from R 1 to R 4 is a single bond bonding to *a,

adjacent two selected from R 1 to R 4 that are not a single bond and R 5 to R 8 do not bond to each other and therefore do not form a cyclic structure,

L 2 represents a single bond, a group of formula (10), or a group of formula (11);

wherein

R 21 to R 26 and R 31 to R 38 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

provided that:

one selected from R 21 to R 26 is a single bond bonding to one selected from R 1 to R 4 via *a, the other one selected from R 21 to R 26 is a single bond bonding to the benzene ring A,

one selected from R 31 to R 38 is a single bond bonding to one selected from R 1 to R 4 via *a, the other one selected from R 31 to R 38 is a single bond bonding to the benzene ring A,

adjacent two selected from R 21 to R 26 that are not a single bond do not bond to each other, and therefore do not form a cyclic structure,

adjacent two selected from R 31 to R 38 that are not a single bond do not bond to each other, and therefore do not form a cyclic structure,

R 41 to R 44 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

a pair of adjacent two selected from R 41 and R 42 , and R 42 and R 43 may bond to each other to form a substituted or unsubstituted benzene ring, or may not bond to each other and therefore may not form a benzene ring;

R 51 to R 55 and R 61 to R 68 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

provided that one selected from R 51 to R 55 is a single bond bonding to *b, one selected from R 61 and R 64 is a single bond bonding to *c,

adjacent two selected from R 51 to R 55 that are not a single bond do not bond to each other and therefore do not form a cyclic structure,

adjacent two selected from R 61 to R 68 that are not a single bond do not bond to each other and therefore do not form a cyclic structure:

L 1 represents a single bond, or a substituted or unsubstituted phenylene group;

Ar represents a group selected from the formulae (20) to (22):

wherein

R 71 to R 75 , R 81 to R 86 , and R 91 to R 95 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

provided that:

one selected from R 71 to R 75 is a single bond bonding to *d,

one selected from R 81 to R 86 is a single bond bonding to *e, the other one selected from R 81 to R 86 is a single bond bonding to *f,

** represents a bonding position to L 1 ,

m is 0,

n is 0,

*f bonds to L 1 ,

adjacent two selected from R 71 to R 75 that are not a single bond, adjacent two selected from R 81 to R 86 that are not a single bond, and adjacent two selected from R 91 to R 95 each independently may bond to each other to form a substituted or unsubstituted cyclic structure or may not bond to each other and therefore may not form a cyclic structure;

the benzene ring B and the benzene ring C, the benzene ring B and the benzene ring D, and the benzene ring C and the benzene ring D do not crosslink;

wherein

R 71 to R 75 , R 81 to R 86 , *d, *e, *f, **, m, and n are as defined in the formula (20),

R 111 to R 118 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

provided that:

one selected from R 111 to R 114 is a single bond bonding to *h;

adjacent two selected from R 111 to R 114 that are not a single bond and R 115 to R 118 each independently may bond to each other to form a substituted or unsubstituted cyclic structure, or may not bond to each other and therefore may not form a cyclic structure;

the benzene ring B and the benzene ring C do not crosslink;

wherein

R 121 to R 128 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

provided that one selected from R 121 to R 124 is a single bond bonding to *i;

X represents CR a R b or an oxygen atom;

one of R a and R b is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, the other is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or R a and R b each are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the two aryl groups may bond to each other via a single bond;

** represents a bonding position to L 1 , and

adjacent two selected from R 121 to R 124 that are not a single bond and R 125 to R 128 each independently may bond to each other to form a substituted or unsubstituted cyclic structure, or may not bond to each other and therefore may not form a cyclic structure.

2 . The compound of claim 1 , wherein R 1 is a single bond bonding to *a.

3 . The compound of claim 1 , wherein R 2 is a single bond bonding to *a.

4 . The compound of claim 1 , wherein R 3 is a single bond bonding to *a.

5 . The compound of claim 1 , wherein R 4 is a single bond bonding to *a.

6 . The compound of claim 1 , wherein R 52 or R 53 is a single bond bonding to *b.

7 . The compound of claim 1 , having formula (2):

wherein

R 1 to R 8 , *a, L 2 , R 41 to R 44 , L 1 , R 51 to R 55 , R 61 to R 68 , *b, and *c are as defined in the formula (1),

Ar 1 is the group of formula (20) or (21).

8 . The compound of claim 1 , wherein Ar or Ar 1 is a substituted or unsubstituted group of formula:

wherein arbitrary substituents are omitted.

9 . The compound of claim 1 , having formula (3):

wherein

R 1 to R 8 , *a, L 2 , R 41 to R 44 , L 1 , R 51 to R 55 , R 61 to R 68 , *b, and *c are as defined in the formula (1),

Ar 2 is the group of formula (22).

10 . The compound of claim 1 , wherein Ar or Ar 2 is a substituted or unsubstituted group of formula:

wherein arbitrary substituents are omitted.

11 . The compound of claim 1 , wherein L 2 is a group of formula (10) or a group of formula (11).

12 . The compound of claim 1 , wherein the compound comprises a deuterium atom.

13 . A material suitable for an organic electroluminescent device, comprising:

the compound of claim 1 .

14 . An organic electroluminescent device, comprising:

a cathode;

an anode; and

organic layers intervening between the cathode and the anode,

wherein the organic layers comprise a light emitting layer, and

wherein at least one layer of the organic layers contains comprises the compound of claim 1 .

15 . The device of claim 14 , wherein the compound comprises a deuterium atom.

16 . The device of claim 14 , wherein the organic layer includes a hole transporting zone between the anode and the light emitting layer, and the hole transporting zone comprises the compound.

17 . The device of claim 16 , wherein the hole transporting zone comprises a first hole transporting layer on the anode side and a second hole transporting layer on the cathode side, and

wherein the first hole transporting layer or the second hole transporting layer or both comprises the compound.

18 . The device of claim 14 , wherein the light emitting layer comprises a fluorescent dopant material.