US 11,718,608 B2
Organic molecules for use in optoelectronic devices
Stefan Seifermann, Bühl (DE)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Appl. No. 16/759,844
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
PCT Filed Oct. 23, 2018, PCT No. PCT/EP2018/079019
§ 371(c)(1), (2) Date Apr. 28, 2020,
PCT Pub. No. WO2019/086297, PCT Pub. Date May 9, 2019.
Claims priority of application No. 17199193 (EP), filed on Oct. 30, 2017.
Prior Publication US 2020/0331898 A1, Oct. 22, 2020
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 V is the binding site of a single bond linking the first chemical moiety to the second chemical moiety;
another one of T or V is R1;
W is R1;
one of X or Y is the binding site of a single bond linking the first chemical moiety to the third chemical moiety;
another one of X or Y is R1;
# represents the binding site of a 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 is 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 a 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,
OSO2R5,
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, 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-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, 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-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, 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;
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, 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-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, 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, 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-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, 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;
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, R3, R4 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, R3, R4 or R5;
wherein the substituents Rf or R5f independently from each other may 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 a single bond linking the first chemical moiety to the third chemical moiety.