Light-emitting device and apparatus including the same

Patent metadata

Field	Value
Publication number	US-2022123234-A1
Application number	US-202117360142-A
Country	US
Kind code	A1
Filing date	Jun 28, 2021
Priority date	Oct 19, 2020
Publication date	Apr 21, 2022
Grant date	—

Abstract

Provided are a light-emitting device and an electronic apparatus including the same. 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, at least one first compound represented by Formula 1, and at least one second compound represented by Formula 2.

First claim

What is claimed is:

1 . A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and comprising an emission layer; at least one first compound represented by Formula 1; and at least one second compound represented by Formula 2:

wherein, in Formulae 1, 2, and 3,
X 11 is O, S, N(R 11a ), or C(R 11a )(R 11b ),
Ar 11 is a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
L 11 , L 12 , and L 31 to L 33 are each independently a single bond, a C 5 -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 ,
a11, a12, and a31 to a33 are each independently an integer from 1 to 3,
Y is C or Si,
Z 1 is no bond, a single bond, O, S, N(R 21a ), or C(R 21a )(R 21b ),
Z 2 is no bond, a single bond, O, S, N(R 22a ), or C(R 22a )(R 22b ),
wherein when Z 1 is O or S, Z 2 is not a single bond,
Ar 21 is a group represented by Formula 3,
b21 is an integer from 1 to 10,
Y 31 is N or C(R 31a ),
Y 32 is N or C(R 32a ),
Y 33 is N or C(R 33a ),
* in Formula 3 indicates a binding site to a neighboring atom,
R 1 to R 8 , R 11 , R 11a , R 11b , R 12 , R 21 , R 21a , R 21b , R 22 , R 22a , R 22b , R 31 , R 32 , R 31a , R 32a , and R 33a 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 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
d11 is an integer from 1 to 10,
d12 is an integer from 1 to 7,
d21 is an integer from 1 to 10,
d22 is an integer from 1 to 9,
the at least one first compound comprises at least one deuterium, and
R 10a is:
deuterium, —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, —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, 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 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), and
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.

2 . The light-emitting device of claim 1 , wherein the emission layer comprises the at least one first compound.

3 . The light-emitting device of claim 1 , wherein the first electrode is an anode,
the second electrode is a cathode, the interlayer further comprises a hole transport region between the emission layer and the first electrode, the interlayer further comprises an electron transport region between the emission layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

4 . The light-emitting device of claim 3 , wherein the electron transport region comprises the at least one second compound.

5 . The light-emitting device of claim 2 , wherein the emission layer further comprises a third compound, and
the third compound is a fluorescent compound or a thermally activated delayed fluorescence (TADF) compound satisfying Equation 1:
Δ E ST =S 1− T 1≤0.3 eV  Equation 1

wherein, in Equation 1, S1 is a lowest excited singlet energy level (eV) of the TADF compound, and T1 is a lowest excited triplet energy level (eV) of the TADF compound.

6 . The organic light-emitting device of claim 4 , further comprising a capping layer outside the second electrode and having a refractive index at a wavelength of 589 nm of equal to or greater than 1.6.

7 . The light-emitting device of claim 2 , wherein the emission layer further comprises a third compound, and
the third compound comprises at least one of compounds represented by Formulae 4-1 to 4-9:

wherein, in Formula 4-1,
A 41 is a C 3 -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 ,
L 41 to L 43 are each independently a single bond, a C 3 -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 ,
a41 to a43 are each independently an integer from 1 to 3,
Ar 41 and Ar 42 are each independently 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 , or a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , and
m41 is an integer from 1 to 6,
in Formulae 4-2 to 4-4,
X 41 to X 45 are each independently a single bond, O, S, N(R 46 ), B(R 46 ), C(R 46 )(R 47 ), or Si(R 46 )(R 47 ),
n41 and n42 are each independently 0, 1, or 2, wherein, when n41 is 0, A 41 and A 42 are not linked to each other, and when n42 is 0, A 44 and A 45 are not linked to each other,
Y 41

Assignees

• Samsung Display Co Ltd

Inventors

• Park Hyejeong

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1011

  Condensed systems · CPC title