US-12628557-B2 - Plurality of host materials and organic electroluminescent device comprising the same

US12628557B2US 12628557 B2US12628557 B2US 12628557B2US-12628557-B2

Abstract

The present disclosure relates to a plurality of host materials comprising at least one first host compound and at least one second host compound, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds according to the present disclosure as host materials, an organic electroluminescent device having a low driving voltage, high luminous efficiency, and long lifespan characteristics can be provided.

Inventors

Hyo-Soon Park
Joon-Hyung Kil
Kyoung-Jin Park
Sang-Hee Cho
So-Mi Park

Assignees

ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.

Dates

Publication Date: 20260512
Application Date: 20220808
Priority Date: 20210909

Claims (9)

1 . A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2: wherein, X 1 and Y 1 each independently represent, —N═, —NR 5 —, —O— or —S—; provided that one of X 1 and Y 1 is —N═, and the other of X 1 and Y 1 is —NR 5 —, —O— or —S—; R 1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar 1 and Ar 2 each independently represent, a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; R 2 to R 5 each independently represent, hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L 2 -N(Ar′)(Ar″); or may be linked to the adjacent substituents to form a ring(s); L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar′ and Ar″ each independently represent, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; a is 1, b and c each independently represent, an integer of 1 or 2, and d represents an integer of 1 to 4; and when b to d are an integer of 2 or more, each of R 2 to R 4 may be the same or different; wherein, R 11 to R 14 each independently represent, *-(L 3 ) e -(Ar 3 ) f , hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to the adjacent substituents to form a ring(s); R 15 to R 22 each independently represent, *-(L 3 ) e -(Ar 3 ) f , hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted tri(C6-C30)arylsilyl; or may be linked to the adjacent substituents to form a ring(s); provided that at least one of R 11 to R 22 is *-(L 3 ) e -(Ar 3 ) f ; L 3 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar 3 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; e represents an integer of 1 to 4, and f represents an integer of 1 or 2; and when e and f are an integer of 2 or more, each of L 3 and each of Ar 3 may be the same or different.
2 . The plurality of host materials according to claim 1 , wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4: wherein, R 1 to R 4 , Ar 1 , Ar 2 , L 1 , and a to d are as defined in claim 1 .
3 . The plurality of host materials according to claim 1 , wherein the formula 2 is represented by any one of the following formulas 2-1 to 2-4: wherein, R 11 to R 22 , L 3 , Ar 3 , e, and f are as defined in claim 1 .
4 . The plurality of host materials according to claim 1 , wherein R 1 , Ar 1 , and Ar 2 of formula 1 each independently represent, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted benzofuropyridyl, a substituted or unsubstituted benzofuropyrimidinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.
5 . The plurality of host materials according to claim 1 , wherein L 3 of formula 2 represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthalenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted triazinylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted quinoxalinylene, a substituted or unsubstituted quinazolinylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted benzoquinoxalinylene.
6 . The plurality of host materials according to claim 1 , wherein a substituted or unsubstituted (3- to 30-membered)heteroaryl of Ar 3 in formula 2 represents a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted dibenzoquinolinyl, a substituted or unsubstituted dibenzoquinazolinyl, a substituted or unsubstituted dibenzoquinoxalinyl, a substituted or unsubstituted indenopyridyl, a substituted or unsubstituted indenopyrimidinyl, a substituted or unsubstituted indenopyrazinyl, a substituted or unsubstituted benzofuropyridyl, a substituted or unsubstituted benzofuropyrimidinyl, a substituted or unsubstituted benzofuropyrazinyl, a substituted or unsubstituted benzothiopyridyl, a substituted or unsubstituted benzothiopyrimidinyl, a substituted or unsubstituted benzothiopyrazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.
7 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 1 is selected from the following compounds:
8 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is selected from the following compounds:
9 . An organic electroluminescent device comprising: a first electrode; a second electrode; and at least one light-emitting layer(s) between the first electrode and the second electrode, wherein the at least one light-emitting layer(s) comprises the plurality of host materials according to claim 1 .

Description

TECHNICAL FIELD The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. BACKGROUND ART An organic electroluminescent device (OLED) was first developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987]. The light-emitting material of an OLED is the most important factor determining luminous efficiency of the device, and may be classified into a host material and a dopant material in a functional aspect. A light-emitting material can be used by mixing a host and a dopant in order to improve color purity, luminous efficiency, and stability. Generally, a device having excellent electroluminescent (EL) characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. When using such a dopant/host material system as a light-emitting material, their selection is important since host materials greatly influence the efficiency and lifespan of the light-emitting device. Generally, a device having excellent electroluminescent (EL) characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. When using such a dopant/host material system as a light-emitting material, their selection is important since host materials greatly influence the efficiency and lifespan of the light-emitting device. Recently, an urgent task is the development of an OLED having high efficiency and long lifespan characteristics. In particular, the development of highly excellent light-emitting material over conventional light-emitting materials is urgently required, considering the EL properties necessary for medium and large-sized OLED panels. U.S. Pat. No. 8,343,637 B2 discloses a compound in which tetramethylphenanthrene is used as a linking group of a carbazole-carbazole compound as an example of a host material. However, the prior art does not disclose a specific device example and a synthesis method thereof, and does not use the same as a hole transport layer material. DISCLOSURE OF THE INVENTION Technical Problem The object of the present disclosure is firstly, to provide a plurality of host materials which is able to produce an organic electroluminescent device having a low driving voltage, high luminous efficiency, and long lifespan characteristics, and secondly, to provide an organic electroluminescent device comprising the host materials. Solution to Problems As a result of intensive studies to solve the technical problem above, the present inventors found that the aforementioned objective can be achieved by a plurality of host materials comprising at least one first host material represented by the following formula 1 and at least one second host material represented by the following formula 2, so that the present invention was completed. in formula 1, X1 and Y1 each independently represent, —N═, —NR5—, —O— or —S—; provided that one of X1 and Y1 is —N═, and the other of X1 and Y, is —NR5—, —O— or —S—;R1 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;Ar1 and Ar2 each independently represent, a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;R2 to R5 each independently represent, hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryisilyl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L2-N(Ar′)(Ar″); or may be linked to the adjacent substituents to form a ring(s);L2 represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroalylene;Ar′ and Ar″ each independently represent, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;a is 1, b and c each independently represent, an integer of 1 or 2, and d represents an integer of 1 to 4; andwhen b to d are an integer of 2 or more, each of R2 to R4 may be the same or different; in formula 2,R11 to R14 each independently represent, *-(L3)e