Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-2022216427-A1
Application number	US-202017604087-A
Country	US
Kind code	A1
Filing date	Apr 17, 2020
Priority date	Apr 25, 2019
Publication date	Jul 7, 2022
Grant date	—

Abstract

Provided is an organic EL device including: a light emitting layer between an anode and a cathode facing each other, in which the light emitting layer contains a first host, a second host, and a luminescent dopant, an indolocarbazole compound represented by General Formula (1) is contained as the first host, and a biscarbazole compound or a dibenzofuran compound having a dibenzofuran or dibenzothiophene ring is contained as the second host. This organic EL device has a low drive voltage, high efficiency, and high drive stability.

First claim

1 . An organic electroluminescent device comprising:
one or more light emitting layers between an anode and a cathode facing each other, wherein at least one light emitting layer contains a first host selected from compounds represented by General Formula (1) below and a second host selected from compounds represented by General Formula (2) or (3) below,

wherein, a ring A is a heterocyclic ring represented by Formula (1a) and condensed with an adjacent ring at an arbitrary position, R's are independently hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms, L 1 , L 2 and L 3 are independently a direct bond, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms, B 1 , B 2 and B 3 independently represent a direct bond or a biphenyldiyl group represented by Formula (1b), at least one of B 1 , B 2 and B 3 is the biphenyldiyl group, and a, b, c, d, and e each independently represent an integer of 0 to 3, and s, t, and u each independently represent an integer of 1 and 2,

wherein, R's independently represent hydrogen, an alkyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an alkoxy group having 2 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 24 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, but are not a carbazole ring group, B 4 's are independently hydrogen, an aromatic hydrocarbon group having 6 to 24 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, the aromatic hydrocarbon group or the aromatic heterocyclic group may have a substituent, j represents an integer of 1 to 6, X's independently represent N, C—R′, or C—, each R′ independently represents hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and a diarylamino group having 12 to 44 carbon atoms, and f, g, h, and i independently represent an integer of 1 to 3, and

wherein, a ring C is a heterocyclic group represented by Formula (3a), L 4 and L 5 are independently a direct bond, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 16 carbon atoms, B 5 and B 6 are a direct bond or an aromatic hydrocarbon group having 6 to 22 carbon atoms, R's are independently hydrogen, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 11 carbon atoms, Y independently represents O or S, m and n are numbers of substitutions and represent integers of 1 to 3, and p and q are numbers of repetitions and are each independently integers of 1 to 4.

2 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (1), B 3 is a biphenyldiyl group represented by Formula (1b).

3 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (1), a, b, and c are 0.

4 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (2), j is an integer of 1 to 3.

5 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (2), X's are N or C—H.

6 . The organic electroluminescent device according to claim 1 ,
wherein Formula (3a) is Formula (4) or (5) below,

where Y is O or S.

7 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (3), L 4 and B 5 are a direct bond.

8 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (3), B 6 is an aromatic hydrocarbon group represented by Formula (6) below.

9 . The organic electroluminescent device according to claim 1 ,
wherein, in General Formula (3), L 5 is an aromatic heterocyclic group represented by Formula (7) below.

10 . The organic electroluminescent device according to claim 1 ,
wherein the compounds represented by General Formula (1) are compounds represented by any one of Formulae (8) to (11) below,

(where B 1 to B 3 , L 1 to L 3 , R, a to f, and s to u have the same meaning as those in General Formula (1).)

11 . The organic electroluminescent device according to claim 1 ,
wherein a proportion of the first host is greater than 20 wt % and less than 55 wt % based on the total amount of the first host and the second host.

12 . The organic electroluminescent device according to claim 1 ,
wherein the light emitting layer contains a luminescent dopant material, and wherein the luminescent dopant material is an organic metal complex containing at least one metal selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.

13 . The organic electroluminescent device according to claim 1 ,
wherein the light emitting layer contains a luminescent dopant material, and wherein the luminescent dopant material is a thermally activated delayed fluorescent dopant material.

14 . The organic electroluminescent device according to claim 1 ,
wherein a hole-blocking layer is provided adjacent to the light emitting layer, and the compound represented by General Formula (1) is contained in the hole-blocking layer.

15 . A method for producing an organic electroluminescent device, the method comprising:
a step of mixing a first host with a second host to prepare a premixture and then vapor-depositing the host material containing the hosts to form a light emitting layer when producing the organic electroluminescent device according to claim 1 .

16 . The method for producing an organic electroluminescent device according to claim 15 ,
wherein a difference in 50% weight reduction temperature between the first host and the second host is within 20° C.

Assignees

• Nippon Steel Chemical & Mat Co Ltd

Inventors

• Ogawa Junya
• Ikenaga Yuji
• Yoshida Kazunari
• Kitahara Ikumi

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D209/86

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

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title