IP Library Granted Patent US 11,611,046
Granted Patent B2
US 11,611,046 · App. 15/125,209 · Granted Mar 21, 2023

Organic electroluminescent device

Inventors: Philipp Stoessel (Frankfurt am Main, DE); Amir Hossain Parham (Frankfurt am Main, DE); Christof Pflumm (Darmstadt, DE); Anja Jatsch (Frankfurt am Main, DE); Joachim Kaiser (Darmstadt, DE)
Assignee: MERCK PATENT GMBH
H01L51/0072C07D471/08C09K11/06H01L51/006H01L51/0054H01L51/0067H01L51/5012H01L51/5028C09K2211/1007C09K2211/1029H01L51/0003H01L51/0004H01L51/0008H01L51/0013H01L51/0056H01L51/0058H01L51/0059H01L51/0077H01L51/5004H01L51/5016H01L51/5206H01L51/5221H01L51/56H01L2251/5376H01L2251/55H01L2251/552
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Quick Facts
Patent No.
US 11,611,046
App. No.
15/125,209
Granted
Mar 21, 2023
Kind
B2
Abstract

The present invention relates to organic electroluminescent devices, the emitting layer thereof containing a blend of a luminescent material having a narrow singlet-triplet gap and a fluorescent emission material having high steric shielding.

Claims (23)

1. An organic electroluminescent device comprising cathode, anode and at least one emitting layer comprising a sterically shielded fluorescent compound, wherein the emitting layer comprises a luminescent organic compound having a gap between the lowest triplet state T 1 and the first excited singlet state S 1 of <0.30 eV (TADF compound), where the peak emission wavelength of the sterically shielded fluorescent compound is greater than or equal to the peak emission wavelength of the TADF compound;

wherein the sterically shielded fluorescent compound comprises a fluorescent base skeleton comprising a rigid n system substituted by one or more sterically demanding substituents, where the sterically demanding substituents are one or more fused-on aliphatic groups of the formulae (Ring-1A) to (Ring-7A)

where the dotted bonds indicate the linkage of the two carbon atoms within the fluorescent base skeleton and in addition:

G is an alkylene group which has 1, 2 or 3 carbon atoms and optionally substituted by one or more R b radicals or an ortho-bonded arylene group which has 5 to 14 aromatic ring atoms and optionally substituted by one or more R b radicals;

R a is in each case independently selected from the group consisting of H, D, F, a straight-chain alkyl group having 1 to 40 carbon atoms and a branched or cyclic alkyl group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R b radicals, an aromatic ring system having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more R b radicals, or an aralkyl group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R o radicals, where it is optionally possible for two or more adjacent R a substituents to form a ring system which may be substituted by one or more R b radicals;

R b is selected from the group consisting of H, D, F, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, and an aromatic ring system having 5 to 30 aromatic ring atoms, where two or more adjacent R b substituents together may form a ring system;

and wherein the emitting layer further comprises at least one matrix compound, which is one or more compounds selected from the group consisting of triarylamines, carbazoles, dibenzofurans, indolocarbazoles, indenocarbazoles, azacarbazoles, bipolar matrix materials, silanes, azaboroles, diazasiloles, diazaphopholes, triazines, pyrimidines, quinoxalines, and bridged carbazoles, with the proviso that the matrix is not a TADF compound;

and wherein T 1 (matrix)−T 1 (TADF)≥0.1 eV,

where T 1 (matrix) and T 1 (TADF) are respectively the lowest triplet energy of the matrix compound and the lowest triplet energy of the TADF compound.

2. The organic electroluminescent device of claim 1 , wherein the peak emission wavelength of the sterically shielded fluorescent compound is at least 10 nm greater than the TADF compound.

3. The organic electroluminescent device as of claim 1 , wherein the TADF compound has a luminescence quantum efficiency of at least 40%.

4. The organic electroluminescent device of claim 1 , wherein the TADF compound has a decay time of ≤50 μs.

5. The organic electroluminescent device of claim 1 , wherein the gap between S 1 and T 1 of the TADF compound is ≤0.25 eV.

6. The organic electroluminescent device of claim 1 , wherein the sterically shielded fluorescent compound has a luminescence quantum efficiency of at least 60%.

7. The organic electroluminescent device of claim 1 , wherein the fluorescent base skeleton is selected from the group consisting of formulae (1) to (70):

where optionally one, two, three or four carbon atoms in the fused aromatic base skeleton in the groups of formulae (1) to (50) are replaced by nitrogen.

8. The organic electroluminescent device of claim 1 , wherein the (Ring-1A) too (Ring-7A) groups do not have any acidic benzylic protons.

9. A process for producing the organic electroluminescent device of claim 1 , comprising applying at least one layer by a sublimation method and/or applying at least one layer by an organic vapor phase deposition method or with the aid of a carrier gas sublimation and/or applying at least one layer from solution, by spin-coating or by a printing method.

10. The organic electroluminescent device of claim 1 , wherein the gap between S 1 and T 1 of the TADF compound is ≤0.15 eV.

11. The organic electroluminescent device of claim 1 , wherein the gap between S 1 and T 1 of the TADF compound is ≤0.10 eV.

12. The organic electroluminescent device of claim 1 , wherein the sterically shielded fluorescent compound has a luminescence quantum efficiency of at least 80%.

13. The organic electroluminescent device of claim 1 , wherein the sterically shielded fluorescent compound has a luminescence quantum efficiency of at least 90%.

14. The organic electroluminescent device of claim 1 , wherein R a in the benzylic positions is not H or D.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Feb 10, 2026
From: MERCK PATENT GMBH
To: UDC IRELAND LIMITED
Reel/Frame 073741/0073 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2016
From: STOESSEL, PHILIPP; PARHAM, AMIR HOSSAIN; PFLUMM, CHRISTOF; JATSCH, ANJA; KAISER, JOACHIM
To: MERCK PATENT GMBH
Reel/Frame 039803/0106 →
Priority Claims (1)
EP 14000911 · Mar 13, 2014 · regional
Continuity (1)
Related Publication 20170077418A1 · Mar 16, 2017