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Luminescent material for delayed fluorescence and organic electroluminescent device comprising the same

專利號(hào)
US11800796B2
公開日期
2023-10-24
申請(qǐng)人
Rohm and Haas Electronic Materials Korea Ltd.
發(fā)明人
Jeong-Hwan Jeon; Hong Yeop Na; Hee-Choon Ahn
IPC分類
H10K85/60; C09K11/06; C07D491/147; C07D403/04; C07D487/04; C07D401/14; C07D413/04; C07D413/14; C07D401/04; C07D471/04; C07D405/04; C07D409/14; C07D403/14; H10K50/11; C07D405/14
技術(shù)領(lǐng)域
c30,c5,or,compound,delayed,membered,heteroaryl,dopant,aryl,seo2
地域: Cheonan

摘要

The present invention relates to a luminescent material for delayed fluorescence and an organic electroluminescent device comprising the same. By using the luminescent material for delayed fluorescence according to the present invention, an organic electroluminescent device having long lifespan, low driving voltage, excellent color purity, and significantly improved luminous efficiency such as current efficiency is provided.

說明書

TECHNICAL FIELD

The present invention relates to a luminescent material for delayed fluorescence and an organic electroluminescent device comprising the same.

BACKGROUND ART

An electroluminescent device (EL device) is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

Generally, an organic electroluminescent device (OLED) has a structure comprising a cathode, an anode, and an organic layer between them. When a voltage is applied, holes are injected from the anode, and electrons are injected from the cathode. Holes and electrons are recombined at a light-emitting layer to form an exciton of high energy. Due to the energy of the exciton, the organic luminescent material transfers to an excited state, and emits light when it returns to a ground state.

An organic light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability. Generally, an EL device having excellent luminous characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. Since host and dopant materials greatly influence the efficiency and lifespan of the EL device when using a dopant/host material system, their selection is important.

權(quán)利要求

1
The invention claimed is:1. An organic electroluminescent device comprising a luminescent material for delayed fluorescence comprising a compound of the following formula 1 as a dopant material, and further comprising a compound of the following formula 8 as a host material:embedded imagewhereinR1 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C5-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or CN; or may be linked to an adjacent substituent to form a substituted or unsubstituted mono- or polycyclic, (C5-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, Si, PO, SO, SO2, and SeO2;X1 represents —CR3 or N;X2 represents —CR6 or N;R3 and R6 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C5-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or CN; or may be linked to an adjacent substituent to form a substituted or unsubstituted mono- or polycyclic, (C5-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, Si, PO, SO, SO2, and SeO2;E is represented by the following formulae 2-1 to 2-5, 2-9 to 2-13, 2-15, 2-19 to 2-28, 2-30, and 2-32 to 2-35;embedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imagewhereinX and Y each independently are selected from O, S, NR4, Si(R4)2, C(R4)2, PO(R4)2, SO, SO2, and SeO2;R4 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C5-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; where there are two R4's, each of the two R4's may be the same or different, and the two R4's may be linked to each other to form a substituted or unsubstituted 11- to 60-membered polycyclic ring; andR each independently represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C5-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; and* represents a bonding site between the ring comprising X1 and X2, and E;independently represents N or CR11;R11 independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C5-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or CN; or may be linked to an adjacent substituent to form a substituted or unsubstituted mono- or polycyclic, (C5-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, Si, PO, SO, SO2, and SeO2;Het represents a 5- to 30-membered heteroaryl(ene);L represents hydrogen, a substituted or unsubstituted (C5-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted mono- or polycyclic, (C5-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, Si, PO, SO, SO2, and SeO2;i represents an integer of 1 or 2; andj represents an integer of 1 to 5; where j is an integer of 2 or more, each of L may be the same or different.2. The organic electroluminescent device comprising the luminescent material for delayed fluorescence according to claim 1, wherein formula 1 is selected from the following formulas 1-1 to 1-16:embedded imageembedded imageembedded imageembedded imagewhereinZ is selected from O, S, NR8, Si(R8)2, C(R8)2, PO(R8)2, SO, SO2, and SeO2;R8 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C5-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; andPh represents phenyl, and E is as defined in claim 1.3. The organic electroluminescent device comprising the luminescent material for delayed fluorescence according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:embedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded image4. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 8 is represented by the following formula 9:embedded imagewhereinX11 independently represents N or CR11;X12 independently represents N or CR12;R11 and R12 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C5-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or CN; or may be linked to an adjacent substituent to form a substituted or unsubstituted mono- or polycyclic, (C5-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, Si, PO, SO, SO2, and SeO2; andL independently represents hydrogen, a substituted or unsubstituted (C5-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted mono- or polycyclic, (C5-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur, Si, PO, SO, SO2, and SeO2.5. The organic electroluminescent device according to claim 4, wherein X12 independently represents N or CH.6. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 8 is selected from the group consisting of:embedded imageembedded imageembedded image
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