Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11569452-B2
Application number	US-201916564265-A
Country	US
Kind code	B2
Filing date	Sep 9, 2019
Priority date	Sep 19, 2018
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

An organic light-emitting device including a predetermined host and a thermally activated delayed fluorescence emitter.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an emission layer disposed between the first electrode and the second electrode,
wherein the emission layer comprises a host and a thermally activated delayed fluorescence emitter,
wherein the emission layer does not comprise a transition metal-containing organometallic compound, and
the host comprises a compound represented by Formula 1, a compound represented by Formula 2, or a combination thereof:

wherein, in Formulae 1 and 2,
Z 1 to Z 6 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, or a cyano group; or
a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, or any combination thereof,
b1 to b6 are each independently 1, 2, 3, or 4, and
in Formulae 1 and 2, at least one of, i) Z 1 in the number of b1, ii) Z 2 in the number of b2, iii) Z 3 in the number of b3, iv) Z 4 in the number of b4, v) Z 5 in the number of b5, and vi) R 6 in the number of b6 is a cyano group.

2. The organic light-emitting device of claim 1 , wherein
Z 1 to Z 6 are each independently:
hydrogen, deuterium, or a cyano group; or
a C 1 -C 10 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, a biphenyl group, or any combination thereof, and
b1 to b6 are each independently 0, 1, or 2.

3. The organic light-emitting device of claim 1 , wherein
the number of a cyano group included in the compound represented by Formula 1 and the number of a cyano group included in the compound represented by Formula 2 are each independently 1, 2, 3, or 4.

4. The organic light-emitting device of claim 1 , wherein
in Formulae 1 and 2,
at least one of, i) Z 1 in the number of b1 and ii) Z 2 in the number of b2 is a cyano group,
at least one of, i) Z 3 in the number of b3 and ii) Z 4 in the number of b4 is a cyano group,
at least one of, i) Z 5 in the number of b5 and ii) Z 6 in the number of b6 is a cyano group,
at least one of, i) Z 1 in the number of b1 and ii) Z 2 in the number of b2 is a cyano group, and at least one of, i) Z 3 in the number of b3 and ii) Z 4 in the number of b4 is a cyano group,
at least one of, i) Z 1 in the number of b1 and ii) Z 2 in the number of b2 is a cyano group, and at least one of, i) Z 5 in the number of b5 and ii) Z 6 in the number of b6 is a cyano group,
at least one of, i) Z 3 in the number of b3 and ii) Z 4 in the number of b4 is a cyano group, and at least one of, i) Z 5 in the number of b5 and ii) Z 6 in the number of b6 is a cyano group, or
at least one of, i) Z 1 in the number of b1 and ii) Z 2 in the number of b2 is a cyano group, at least one of, i) Z 3 in the number of b3 and ii) Z 4 in the number of b4 is a cyano group, and at least one of, i) Z 5 in the number of b5 and ii) Z 6 in the number of b6 is a cyano group.

5. The organic light-emitting device of claim 1 , wherein
a group represented by

in Formula 1 is a group represented by one of Formulae PO1 to PO25,
a group represented by

in Formula 2 is a group represented by one of Formulae PM1 to PM25:

wherein, in Formulae PO1 to PO25 and PM1 to PM25,
Z 10 to Z 19 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, or a cyano group; or
a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, or any combination thereof, and
* and *′ each indicate a binding site to a neighboring nitrogen atom.

6. The organic light-emitting device of claim 1 , wherein
a group represented by

in Formulae 1 and 2 is a group represented by one of Formulae A1-1 to A1-3,
a group represented by

in Formulae 1 and 2 is a group represented by one of Formulae A2-1 to A2-3:

wherein, in Formulae A1-1 to A1-3 and A2-1 to A2-3,
Z 21 to Z 28 and Z 31 to Z 38 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, or a cyano group; or
a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, or any combination thereof, and
* and *′ each indicate a binding site to a neighboring atom.

7. The organic light-emitting device of claim 1 , wherein the host comprises at least one of Compounds EH1 to EH15:

8. The organic light-emitting device of claim 1 , wherein
the compound represented by Formula 1 and the compound represented by Formula 2 each have a dipole moment of about 6.4 debye or more.

9. The organic light-emitting device of claim 1 , wherein
a difference between a triplet energy level of the thermally activated delayed fluorescence emitter and a singlet energy level of the thermally activated delayed fluorescence emitter is greater than or equal to about 0 eV to less than or equal to about 0.5 eV, and
the triplet energy level and the singlet energy level are each evaluated by using a density functional theory method of a Gaussian program that is structurally optimized at a level of B3LYP/6-31 G(d,p).

10. The organic light-emitting device of claim 1 , wherein the thermally activated delayed fluorescence emitter comprises a compound represented by Formula 11:

wherein, in Formula 11,
X 1 is a single bond, N-[(L 4 ) c4 -R 4 ], C(R 5 )(R 6 ), O, or S,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Ihn Sooghang
• Jeong Daun
• Sim Myungsun
• Lee Hasup
• Kwon Eunsuk
• Kim Sangmo
• Min Minsik
• Park Sangho
• Jeon Soonok
• Chung Yeonsook

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• H01L2251/5384

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic

• C07D209/88 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title