Heterocyclic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device

Patent metadata

Field	Value
Publication number	US-12402525-B2
Application number	US-202117452318-A
Country	US
Kind code	B2
Filing date	Oct 26, 2021
Priority date	Oct 29, 2020
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

Provided is a heterocyclic compound represented by Formula 1, a light-emitting device including the same, and an electronic apparatus including the light-emitting device. The light-emitting device includes a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, and the heterocyclic compound represented by Formula 1.

First claim

What is claimed is:

1. A heterocyclic compound represented by Formula 1:

wherein, in Formula 1,
EW 11 is —CN,
d1 is 0 or 1,
wherein EW 1 in Formula 1 is an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzoisothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an acridine group, or a pyridopyrazine group, or
T 1 is a group represented by Formula 2, and
b1 is an integer from 1 to 5,
wherein, in Formula 2,
X 1 is O or S,
L 1 is a single bond, a C 4 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
a1 is an integer from 0 to 5, and
Ar 1 and Ar 2 are each independently a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , and
wherein, in Formulae 1 and 2,
R 1 and R 2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), or —C(═O)(Q 1 ),
c1 in Formula 1 is an integer from 0 to 10, c2 in Formula 2 is an integer from 0 to 7, and
R 10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -Coo aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ),
wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently:
hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
* in Formula 2 indicates a binding site to EW 1 in Formula 1, and
wherein when d1 is 0, either (i) b1 is an integer from 2 to 5, or (ii) c1 in Formula 1 is an integer from 2 to 10 and at least one R 1 is a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a and at least one other R 1 is a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a .

2. The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by Formula 1(a) or 1(b):

wherein, in Formulae 1(a) and 1(b),
X 11 is N or C(R 11 ),
X 12 is N or C(R 12 ),
X 13 is N or C(R 13 ),
at least one selected from X 11 to X 13 is N or C(CN),
R 11 to R 15 are the same as described in connection with R 1 , and
T 11 and T 12 are the same as described in connection with T 1 .

3. A heterocyclic compound represented by Formula 1(a) or 1(b):

wherein, in Formulae 1(a) and 1(b),
X 11 is N or C(R 11 ),
X 12 is N or C(R 12 ),
X 13 is N or C(R 13 ),
T 11 and T 12 are each a group represented by Formula 2, and
wherein, in Formula 2,
X 1 is O or S,
L 1 is a single bond, a C 4 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
a1 is an integer from 0 to 5, and
Ar 1 and Ar 2 are each independently a Ir electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , and
wherein, in Formulae 1(a), 1(b), and 2,
R 2 and R 11 to R 15 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), or —C(═O)(Q 1 ), wherein at least one of R 11 to R 15 is a C 3 -C 60 carboxylic group unsubstituted or substituted with at least one R 10a and at least one other of R 11 to R 15 is a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
c2

Assignees

• Samsung Display Co Ltd
• Nat Univ Gyeongsang Iacf

Inventors

• Um Hyunah
• Kim Yunhi
• Kwon Soonki
• Ahn Heechoon
• Park Jihyun

Classifications

• H10K59/40

  OLEDs integrated with touch screens · CPC title

• H10K59/38

  comprising colour filters or colour changing media [CCM] · CPC title

• H10K59/123

  Connection of the pixel electrodes to the thin film transistors [TFT] · CPC title

• H10K50/844

  Encapsulations · CPC title

• H10K50/12

  comprising dopants · CPC title