Mixture, thin film, and organic light emitting device including mixture and thin film

Patent metadata

Field	Value
Publication number	US-10297764-B2
Application number	US-201615262584-A
Country	US
Kind code	B2
Filing date	Sep 12, 2016
Priority date	Sep 14, 2015
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

A composition including a donor compound and an acceptor compound, wherein the donor compound and the acceptor compound form an exciplex having characteristics described in the specification.

First claim

What is claimed is:

1. A composition comprising:
a donor compound and an acceptor compound,
wherein the donor compound and the acceptor compound form an exciplex,
wherein a maximum emission wavelength λ max (Ex) in a photoluminescence spectrum of the exciplex is about 390 nanometers or greater and about 490 nanometers or less,
wherein a decay time T decay (Ex) of delayed fluorescence in a time-resolved photoluminescence spectrum of the exciplex is about 100 nanoseconds or greater,
wherein a ratio of a delayed fluorescence portion to the overall light-emitting portions in the time-resolved photoluminescence spectrum of the exciplex is about 10% or greater,
wherein a photoluminescence stability of the exciplex is 60% or greater,
wherein the photoluminescence spectrum and the time-resolved photoluminescence spectrum of the exciplex are each a spectrum measured at room temperature with respect to a film that is formed by co-deposition of the donor compound and the acceptor compound on a substrate, and
wherein the photoluminescence stability of the exciplex is calculated according to Equation 10:
PL stability (%)=( I 2 /I 1 )×100  Equation 10

wherein, in Equation 10,
I 1 is an intensity of a light at the maximum emission wavelength λ max (Ex) in a photoluminescence spectrum of Film 1, which is obtained immediately after formation of a film by co-deposition of the donor compound and the acceptor compound on a substrate, measured at room temperature in an inert atmosphere in which external air is excluded, and
I 2 is an intensity of a light at the maximum emission wavelength λ max (Ex) in a photoluminescence spectrum of Film 2, which is obtained after exposure of the Film 1 to pumping laser light used in the evaluation of I 1 in an inert atmosphere in which external air is excluded for 3 hours, measured at room temperature in an inert atmosphere in which external air is excluded.

2. The composition of claim 1 , wherein the maximum emission wavelength λ max (Ex) is about 390 nanometers or greater and about 440 nanometers or less.

3. The composition of claim 1 , wherein
an absolute value of the highest occupied molecular orbital energy level of the donor compound |HOMO (D)| is about 5.78 electron volts or less,
an absolute value of the lowest unoccupied molecular orbital energy level of the acceptor compound |LUMO (A)| is about 1.76 electron volts or greater,
the highest occupied molecular orbital energy level of the donor compound is calculated by using cyclic voltammetry, and
the lowest unoccupied molecular orbital energy level of the acceptor compound is calculated by using an ultraviolet absorption spectrum measured at room temperature.

4. The composition of claim 1 , wherein
an absolute value of the highest occupied molecular orbital energy level difference between the acceptor compound and the donor compound |HOMO (A)−HOMO (D)| is about 0.037 electron volts or greater and about 1.1 electron volts or less,
an absolute value of the lowest unoccupied molecular orbital energy level difference between the acceptor compound and the donor compound |LUMO (A)−LUMO (D)| is about 0.001 electron volts or greater and about 1.1 electron volts or less,
the highest occupied molecular orbital energy level of the donor compound is calculated by using cyclic voltammetry, and
the lowest unoccupied molecular orbital energy level of the acceptor compound is calculated by using an ultraviolet absorption spectrum measured at room temperature.

5. The composition of claim 1 , wherein
the donor compound comprises at least one selected from a carbazole-containing ring, a dibenzofuran-containing ring, a dibenzothiophene-containing ring, an indenocarbazole-containing ring, an indolocarbazole-containing ring, a benzofurocarbazole-containing ring, a benzothienocarbazole-containing ring, an acridine-containing ring, a dihydroacridine-containing ring, and a tri-indolobenzene-containing ring, and
the acceptor compound comprises at least one selected from a carbazole-containing ring, a dibenzofuran-containing ring, a dibenzothiophene-containing ring, an indenocarbazole-containing ring, an indolocarbazole-containing ring, a benzofurocarbazole-containing ring, a benzothienocarbazole-containing ring, a pyridine-containing ring, a pyrimidine-containing ring, and a triazine-containing ring.

6. The composition of claim 1 , wherein
the donor compound does not comprise an electron withdrawing group, and
the acceptor compound comprises at least one electron withdrawing group,
wherein the electron withdrawing group is selected from
—F, —CFH 2 , —CF 2 H, —CF 3 , —CN, and —NO 2 ;
a C 1 -C 60 alkyl group substituted with at least one selected from —F, —CFH 2 , —CF 2 H, —CF 3 , —CN, and —NO 2 ;
a C 1 -C 60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group, each comprising *═N—*′ as a ring-forming moiety; and
a C 1 -C 60 heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group, each comprising *═N—*′ as a ring-forming moiety and each substituted with at least one selected from deuterium, —F, —CFH 2 , —CF 2 H, —CF 3 , —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

7. The composition of claim 1 , wherein
the donor compound is selected from a compound represented by Formula D-1, and
the acceptor compound is selected from compounds represented by Formulae A-1 and A-2:

wherein, in Formulae D-1, A-1, A-2, and 11 to 14,
Ar 1 is selected from groups represented by Formulae 11 and 12,
Ar 2 is selected from
groups represented by Formulae 11 and 12, a phenyl group, and a naphthyl group; and
a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
Ar 11 and Ar 12 are each independently selected from groups represented by Formulae 13 and 14,
X 1 is N or C(T 14 ), X 2 is N or C(T 15 ), X 3 is N or C(T 16 )

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Ihn Sooghang
• Kang Hosuk
• Son Jhunmo
• Lee Namheon
• Kim Jongsoo
• Kim Joonghyuk
• Sim Myungsun
• Son Youngmok
• Jeon Soonok
• Huh Dalho

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/5206

  Electricity · mapped topic

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H01L51/5012

  Electricity · mapped topic

• H01L2251/552

  Electricity · mapped topic