US 12,187,711 B2
Organic molecules for use in optoelectronic devices
Stefan Seifermann, Bühl (DE)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed on May 8, 2023, as Appl. No. 18/314,060.
Application 18/314,060 is a division of application No. 16/759,844, granted, now 11,718,608, previously published as PCT/EP2018/079019, filed on Oct. 23, 2018.
Claims priority of application No. 17199193 (EP), filed on Oct. 30, 2017.
Prior Publication US 2023/0278992 A1, Sep. 7, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 409/14 (2006.01); C07D 403/14 (2006.01); C07D 405/14 (2006.01); H10K 85/60 (2023.01)
CPC C07D 409/14 (2013.01) [C07D 403/14 (2013.01); C07D 405/14 (2013.01); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 20 Claims
 
1. An organic molecule, consisting of:
one first chemical moiety represented by a structure of Formula I:

OG Complex Work Unit Chemistry
one second chemical moiety represented by a structure of Formula II:

OG Complex Work Unit Chemistry
wherein the first chemical moiety is linked to the second chemical moiety via a single bond; and
one third chemical moiety represented by a structure of Formula III:

OG Complex Work Unit Chemistry
wherein the first chemical moiety is linked to the third chemical moiety via a single bond;
wherein
one of T or W is a binding site of the single bond linking the first chemical moiety to the second chemical moiety;
another one of T or W is R1;
one of X, V or Y is a binding site of the single bond linking the first chemical moiety to the third chemical moiety;
other two of X, V or Y are each independently R1;
#represents the binding site of the single bond linking the first chemical moiety to the second chemical moiety;
A is selected from the group consisting of O, S and N-Ph;
Z is a direct bond;
RN is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
C1-C5-alkyl, wherein one or more hydrogen atoms of the C1-C5-alkyl are optionally substituted by deuterium;
C2-C8-alkenyl, wherein one or more hydrogen atoms of the C2-C8-alkenyl are optionally substituted by deuterium;
C2-C8-alkynyl, wherein one or more hydrogen atoms of the C2-C8-alkynyl are optionally substituted by deuterium;
C6-C18-aryl, which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl, which is optionally substituted with one or more substituents R6:
RI, RII, RIII, and RIV are at each occurrence independently from another selected from the group consisting of $ and Rd;
Rd is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
C6-C18-aryl, which is optionally substituted with one or more substituents independently from another selected from the group consisting of:
C1-C5-alkyl, wherein optionally one or more hydrogen atoms of the C1-C5-alkyl are independently from each other substituted by deuterium, CN, CF3, or F; and
C6-C18-aryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
$ represents the binding site of the single bond linking the first chemical moiety to the third chemical moiety;
R1 is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
C1-C5-alkyl, wherein one or more hydrogen atoms of the C1-C5-alkyl are optionally substituted by deuterium;
C2-C8-alkenyl, wherein one or more hydrogen atoms of the C2-C8-alkenyl are optionally substituted by deuterium;
C2-C8-alkynyl, wherein one or more hydrogen atoms of the C2-C8-alkynyl are optionally substituted by deuterium; and
C6-C18-aryl, which is optionally substituted with one or more substituents independently from another selected from the group consisting of:
C1-C5-alkyl, wherein optionally one or more hydrogen atoms of the C1-C5-alkyl are independently from each other substituted by deuterium, CN, CF3, or F; and
C6-C18-aryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
Ra is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
N(R5)2,
OR5,
Si(R5)3,
B(OR5)2,
R5,
CF3,
CN,
F,
Br,
I,
C1-C40-alkyl,
which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CEC, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C=S, C=Se, C=NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C1-C40-alkoxy,
which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C=C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C=S, C=Se, C=NR5 P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C=C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C=S, C=Se, C=NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C2-C40-alkenyl,
which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C=C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C=S, C=Se, C=NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C2-C40-alkynyl,
which is optionally substituted with one or more substituents R5 and wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C=C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C=S, C=Se, C=NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C6-C60-aryl, which is optionally substituted with one or more substituents R5 and
C3-C57-heteroaryl, which is optionally substituted with one or more substituents R5;
R5 is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
N(R6)2,
OR6,
Si(R6)3,
B(OR6)2,
OSO2R6,
CF3,
CN,
F,
Br,
I,
C1-C40-alkyl,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C=C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6 P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C1-C40-alkoxy,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C=C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CEC, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C2-C40-alkenyl,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C=C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C2-C40-alkynyl,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CEC, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C6-C60-aryl, which is optionally substituted with one or more substituents R6; and
C3-C57-heteroaryl, which is optionally substituted with one or more substituents R6;
Rf is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
N(R5f)2,
OR5f,
Si(R5f)3,
B(OR5f)2,
OSO2R5f,
CF3,
CN,
F,
Br
I,
C1-C40-alkyl,
which is optionally substituted with one or more substituents R5f and wherein one or more non-adjacent CH2-groups are optionally substituted by R5fC=CR5f, C=C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C=S, C=Se, C=NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S or CONR5f,
C1-C40-alkoxy,
which is optionally substituted with one or more substituents R5f and wherein one or more non-adjacent CH2-groups are optionally substituted by R5fC=CR5f, CEC, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C=S, C=Se, C=NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S or CONR5f;
C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R5f and wherein one or more non-adjacent CH2-groups are optionally substituted by R5fC=CR5f, C=C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C=S, C=Se, C=NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S or CONR5f,
C2-C40-alkenyl,
which is optionally substituted with one or more substituents R5f and wherein one or more non-adjacent CH2-groups are optionally substituted by R5fC=CR5f, C=C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C=S, C=Se, C=NR5f, P(═O)(R5f), SO, SO2, NR5f, O, S or CONR5f,
C2-C40-alkynyl,
which is optionally substituted with one or more substituents R5f and wherein one or more non-adjacent CH2-groups are optionally substituted by R5fC=CR5f, C=C, Si(R5f)2, Ge(R5f)2, Sn(R5f)2, C═O, C=S, C=Se, C=NR5f P(═O)(R5f), SO, SO2, NR5f, O, S or CONR5f;
C6-C60-aryl, which is optionally substituted with one or more substituents R5f, and
C3-C57-heteroaryl, which is optionally substituted with one or more substituents R5f;
R5f is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
N(R6)2,
OR6,
Si(R6)3,
B(OR6)2,
OSO2R6
CF3,
CN,
F,
Br,
I,
C1-C40-alkyl,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CEC, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C1-C40-alkoxy,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, C=C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CEC, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6 P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C2-C40-alkenyl,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CEC, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C=S, C=Se, C=NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C2-C40-alkynyl,
which is optionally substituted with one or more substituents R6 and wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, CEC, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6 P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C6-C60-aryl, which is optionally substituted with one or more substituents R6; and
C3-C57-heteroaryl, which is optionally substituted with one or more substituents R6;
R6 is at each occurrence independently from another selected from the group consisting of:
hydrogen,
deuterium,
OPh,
CF3,
CN,
F,
C1-C5-alkyl, wherein optionally one or more hydrogen atoms of the C1-C5-alkyl are independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-alkoxy, wherein optionally one or more hydrogen atoms of the C1-C5-alkoxy are independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-thioalkoxy, wherein optionally one or more hydrogen atoms of the C1-C5-thioalkoxy are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl, wherein optionally one or more hydrogen atoms of the C2-C5-alkenyl are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl, wherein optionally one or more hydrogen atoms of the C2-C5-alkynyl are independently from each other substituted by deuterium, CN, CF3, or F;
C6-C18-aryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
C3-C17-heteroaryl, which is optionally substituted with one or more C1-C5-alkyl substituents;
N (C6-C18-aryl)2;
N (C3-C17-heteroaryl)2; and
N (C3-C17-heteroaryl) (C6-C18-aryl);
wherein the substituents Ra or R5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents Ra or R5;
wherein the substituents Rf or R5f independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents Rf or R5f; and
wherein exactly one substituent selected from the group consisting of RI, RII, RIII and RIV is the binding site of the single bond linking the first chemical moiety to the third chemical moiety.