公开(公告)号：US12274168B2

公开(公告)日：2025-04-08

申请号：US17287406

申请日：2019-10-24

Applicant: IDEMITSU KOSAN CO., LTD.

Inventor： Keiichi Yasukawa ,  Shota Sawano ,  Hiromi Nakano ,  Takushi Shiomi

IPC: H10K85/60 ,  C07D209/80 ,  C07D487/04 ,  C07D491/048 ,  C07D491/147 ,  C07D495/04 ,  C09K11/06 ,  H10K50/11 ,  H10K50/12 ,  H10K101/20

Abstract: A compound is represented by a formula (1). n is 2 to 4, m is 1 to 4, q is 0 to 3, and m+n+q=6; CN is a cyano group; D1 is a group represented by a formula (2), (3) or (3X), the plurality of D1 are the same; and Rx is a hydrogen atom or substituent. R1 to R8 are each independently a hydrogen atom or substituent. R31 to R38 and R41 to R48 are each independently a hydrogen atom or substituent; p, px and py are each independently 1 to 4; A to C are each independently a cyclic structure represented by a formula (131) or (132). R19 and R20 are each independently a hydrogen atom or substituent. X1 is a sulfur atom or the like, and * represents a bonding position with a carbon atom of a benzene ring in the formula (1).

公开(公告)号：US12075699B2

公开(公告)日：2024-08-27

申请号：US17764846

申请日：2021-01-22

Applicant: IDEMITSU KOSAN CO.,LTD.

Inventor： Takushi Shiomi ,  Toshinari Ogiwara ,  Hiromi Nakano

IPC: H01L51/50 ,  C07D209/86 ,  C07D405/10 ,  C07D405/14 ,  C07D491/048 ,  C07D495/04 ,  C09K11/06 ,  H10K85/60 ,  H10K50/11

CPC classification number: H10K85/6572 ,  C07D209/86 ,  C07D405/10 ,  C07D405/14 ,  C07D491/048 ,  C07D495/04 ,  C09K11/06 ,  H10K85/654 ,  H10K85/657 ,  H10K85/6574 ,  C07B2200/05 ,  C09K2211/1018 ,  H10K50/11

Abstract: An organic electroluminescence device includes an anode, an emitting layer, and a cathode in this order. The emitting layer comprises a delayed fluorescent compound M2 and a compound M3 having at least one deuterium atom, and the compound M3 is not a compound having a partial structure represented by a formula (1C) or (2C). S1(M2) of the compound M2 and S1(M3) of the compound M3 satisfy a relationship of S1(M3)>S1(M2). In the formulae (1C) and (2C), Y41 to Y48 are each independently a N atom, CR, or a C atom bonded to another atom or the like in the compound M3, where each R is independently a H atom or a substituent, at least one of Y41 to Y48 is a N atom, and at least one of Y41 to Y48 is a C atom bonded to another atom or the like in the compound M3.

公开(公告)号：US12289995B2

公开(公告)日：2025-04-29

申请号：US17236029

申请日：2021-04-21

Applicant: IDEMITSU KOSAN CO.,LTD.

Inventor： Hiromi Nakano ,  Hisato Matsumoto ,  Yuichi Nishimae

IPC: H01L51/00 ,  C07F5/02 ,  H10K85/60 ,  H10K50/11

Abstract: A compound is represented by a formula (1). In the formula (1), at least one combination of adjacent two or more of R1 to R17 are mutually bonded to form a ring represented by a formula (2), in which RX1 to RX4 and R1 to R17 are each independently a hydrogen atom, a substituent or the like,

公开(公告)号：US12157747B2

公开(公告)日：2024-12-03

申请号：US17413248

申请日：2019-12-11

Applicant: IDEMITSU KOSAN CO., LTD.

Inventor： Takushi Shiomi ,  Hiromi Nakano

IPC: C07D519/00 ,  H10K85/60 ,  H10K50/11 ,  H10K101/10

Abstract: An organic EL device includes an anode, a cathode, and an emitting layer interposed between the anode and the cathode, in which the emitting layer includes a delayed fluorescent compound M2 and a compound M3 represented by a formula (100), and a singlet energy S1(M2) of the compound M2 and a singlet energy S1(M3) of the compound M3 satisfy a numerical formula (Numerical Formula 1). In the formula (100), X1 is an oxygen atom or a sulfur atom, C1 is a carbon atom, R11 to R18, R2, R31, R32, R34, R35, R4 and R45 to R48 are each independently a hydrogen atom, substituent or the like, n is 1, 2, or 3. When L1 is a single bond, n is 1, k is 1, 2, or 3, m is 2, 3, or 4, k+m=5, and L1 is a single bond or linking group.

公开(公告)号：US12302757B2

公开(公告)日：2025-05-13

申请号：US18774623

申请日：2024-07-16

Applicant: IDEMITSU KOSAN CO., LTD.

Inventor： Takushi Shiomi ,  Toshinari Ogiwara ,  Hiromi Nakano

IPC: H10K85/60 ,  C07D209/86 ,  C07D405/10 ,  C07D405/14 ,  C07D491/048 ,  C07D495/04 ,  C09K11/06 ,  H10K50/11

Abstract: A compound may include partial structures of formula (3-11B) and (31a) in one molecule: R314 being a single bond bonded to * in formula (31a), R300 being independently H or a substituent, or at least one of adjacent pairs of R300 are mutually bonded to form a ring, or R300 is a single bond bonded to another atom/structure in the molecule, one or more R300 is H, at least one of H being D, Y12 to Y16 being independently N, CR31, or C bonded to another atom/structure in the molecule, 1 to 3 of Y12 to Y16 being N, and R31 independently being H or a substituent.

公开(公告)号：US12029120B2

公开(公告)日：2024-07-02

申请号：US18537181

申请日：2023-12-12

Applicant: IDEMITSU KOSAN CO., LTD.

Inventor： Takushi Shiomi ,  Toshinari Ogiwara ,  Hiromi Nakano

IPC: H01L51/50 ,  C07D209/86 ,  C07D405/10 ,  C07D405/14 ,  C07D491/048 ,  C07D495/04 ,  C09K11/06 ,  H10K85/60 ,  H10K50/11

CPC classification number: H10K85/6572 ,  C07D209/86 ,  C07D405/10 ,  C07D405/14 ,  C07D491/048 ,  C07D495/04 ,  C09K11/06 ,  H10K85/654 ,  H10K85/657 ,  H10K85/6574 ,  C07B2200/05 ,  C09K2211/1018 ,  H10K50/11

Abstract: An organic electroluminescence device includes an anode, an emitting layer, and a cathode in this order. The emitting layer contains a compound, including a structure including a first partial structure of formula (3-100) and a second partial structure of formula (3-1A), mutually bonded in one molecule:




In formula (3-100), D1 to D3 are each a deuterium atom, or one of D1 to D8 is a single bond to another atom/structure in the molecule, and remaining D1 to D8 are each a deuterium atom, and R310 is a single bond bonded to the second partial structure. In formula (3-1A), one of R301 to R306 is a single bond bonded to the first partial structure, and remaining R301 to R306 not being bonded to the first partial structure are independently H, a substituent, or a single bond bonded to another atom/structure in the molecule.

公开(公告)号：US12250883B2

公开(公告)日：2025-03-11

申请号：US18668609

申请日：2024-05-20

Applicant: IDEMITSU KOSAN CO.,LTD.

Inventor： Takushi Shiomi ,  Toshinari Ogiwara ,  Hiromi Nakano

IPC: H01L51/50 ,  C07D209/86 ,  C07D405/10 ,  C07D405/14 ,  C07D491/048 ,  C07D495/04 ,  C09K11/06 ,  H10K85/60 ,  H10K50/11

Abstract: A compound may include a partial structures of formula (3-1A), (32h), and (3-11B) in one molecule, R300 to R306 being independently H or a substituent, or adjacent pair(s) form a ring, at least one of R301 to R306 is a single bond to another atom/structure in the molecule, and one of R301 to R306 is a single bond to the partial structure of formula (32h), X30 is N bonded to the partial structure of formula (3-1A), Y41 to Y48 are independently CR32, or C bonded to another atom/structure in the molecule, at least one of Y41 to Y48 is C bonded to the partial structure of formula (3-11B), R32 are independently H or a substituent, or pair(s) of adjacent R32 are bonded to form a ring, and at least one R32 is independently a single bond to another atom/structure in the molecule.

公开(公告)号：US12127478B2

公开(公告)日：2024-10-22

申请号：US17345450

申请日：2021-06-11

Applicant: IDEMITSU KOSAN CO.,LTD.

Inventor： Takushi Shiomi ,  Hisato Matsumoto ,  Hiromi Nakano ,  Toshinari Ogiwara

IPC: H01L51/50 ,  H10K71/16 ,  H10K85/40 ,  H10K85/60 ,  H10K50/11 ,  H10K101/00 ,  H10K101/10

CPC classification number: H10K85/6572 ,  H10K71/164 ,  H10K85/40 ,  H10K85/631 ,  H10K85/6565 ,  H10K85/6574 ,  H10K85/6576 ,  H10K50/11 ,  H10K2101/10 ,  H10K2101/90

Abstract: An organic EL device includes an anode, a cathode, and an emitting layer. The emitting layer contains a first compound represented by a formula (1X) or a formula (1Y), a second compound, and a third compound that exhibits delayed fluorescence. The second compound is different in structure from the first compound. The second compound is different in structure from the third compound. Singlet energies S1 of the first, second, third compounds satisfy Numerical Formula 1 and Numerical Formula 2 below,




A is, for example, a group represented by a formula (a1); Y11˜Y13 are, for example, each independently a nitrogen atom or CRy; Ry is, for example, a substituent or a group represented by a formula (1Z); R1X to R3X are, for example, each independently a substituent or a group represented by a formula (1Z).