IP Library Granted Patent US 12673932
Granted Patent B2
US 12673932 · App. 17/600,149 · Granted Jul 7, 2026

Heterocyclic compound and organic light emitting device comprising same

Inventors: Young-Jin Lee (Yongin-si, KR); Seong-Jong Park (Yongin-si, KR); Won-Jang Jeong (Yongin-si, KR); Dong-Jun Kim (Yongin-si, KR)
Assignee: LT MATERIALS CO., LTD.
C07D401/14C09K11/06H10K50/18H10K85/654H10K85/6572C09K2211/1018H10K50/16H10K50/17H10K50/19
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Quick Facts
Patent No.
US 12673932
App. No.
17/600,149
Granted
Jul 7, 2026
Kind
B2
Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device including the same.

Claims (41)

1 . An organic light emitting device comprising:

a first electrode;

a second electrode; and

an organic material layer provided between the first electrode and the second electrode,

wherein the organic material layer includes an electron transfer layer, a hole blocking layer or a charge generation layer,

at least one of the electron transfer layer, the hole blocking layer and the charge generation layer includes one or more types of a heterocyclic compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,

R1 is hydrogen; or deuterium,

R2 is hydrogen; deuterium; or a phenyl group, or a plurality of R2s bond to each other to form a benzene ring,

R3 is hydrogen; deuterium; or a phenyl group, or a plurality of R3s bond to each other to form a benzene ring,

L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group; or a biphenylene group,

Z1 is —P(═O)(R104′)(R105′); a phenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; a biphenyl group; a terphenyl group; a naphthyl group; an anthracenyl group; a phenanthrenyl group unsubstituted or substituted with an aryl group; a pyrenyl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; a fluoranthenyl group; a pyrimidine group unsubstituted or substituted with an aryl group; a triazine group unsubstituted or substituted with an aryl group; a quinazolinyl group unsubstituted or substituted with an aryl group; a carbazole group unsubstituted or substituted with an aryl group; a phenanthrolinyl group unsubstituted or substituted with an aryl group; a phenanthridinyl group unsubstituted or substituted with an aryl group; a benzophenanthridinyl group; a dibenzofuran group; a dibenzothiophene group; dibenzosulfolane; spiro[fluorene-9,9′-xanthene]; a benzo[4,5]thieno[3,2-d]pyrimidyl group unsubstituted or substituted with an aryl group; a benzofuro[2,3-c]quinolinyl group; a benzofuro[3,2-c]quinolinyl group; a benzothieno[2,3-c]quinolinyl group; a benzothieno[3,2-c]quinolinyl group; or a pyrazolo[5,1-a]isoquinolinyl group unsubstituted or substituted with an aryl group, and R104′ and R105′ are each independently an aryl group,

Z2 and Z3 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a methyl group; a pyrimidine group unsubstituted or substituted with an aryl group; a triazine group unsubstituted or substituted with an aryl group; or a carbazole group,

R104 and R105 are each independently a phenyl group,

r1 and r2 are each an integer of 1 to 3,

r3 is an integer of 1 to 4,

l1 to l3 and z′1 to z′3 are each independently an integer of 1 to 5, and

when r1 to r3, l1 to l3 and z′1 to z′3 are each 2 or greater, substituents in the parentheses are the same as or different from each other.

2 . The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-4:

in Chemical Formulae 1-1 to 1-4,

r1 to r3, l1 to l3 and z′1 to z′3 have the same definitions as in Chemical Formula 1,

R11 is hydrogen; or deuterium,

R12 is hydrogen; deuterium; or a phenyl group, or a plurality of R12s bond to each other to form a benzene ring,

R13 is hydrogen; deuterium; or a phenyl group, or a plurality of R13s bond to each other to form a benzene ring,

L11 to L13 are the same as or different from each other, and each independently a direct bond; a phenylene group; or a biphenylene group,

Z11 is —P(═O)R(104′)(R105′); a phenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; a biphenyl group; a terphenyl group; a naphthyl group; an anthracenyl group; a phenanthrenyl group unsubstituted or substituted with an aryl group; a pyrenyl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; a fluoranthenyl group; a pyrimidine group unsubstituted or substituted with an aryl group; a triazine group unsubstituted or substituted with an aryl group; a quinazolinyl group unsubstituted or substituted with an aryl group; a carbazole group unsubstituted or substituted with an aryl group; a phenanthrolinyl group unsubstituted or substituted with an aryl group; a phenanthridinyl group unsubstituted or substituted with an aryl group; a benzophenanthridinyl group; a dibenzofuran group; a dibenzothiophene group; dibenzosulfolane; spiro[fluorene-9,9′-xanthene]; a benzo[4,5]thieno[3,2-d]pyrimidyl group unsubstituted or substituted with an aryl group; a benzofuro[2,3-c]quinolinyl group; a benzofuro[3,2-c]quinolinyl group; a benzothieno[2,3-c]quinolinyl group; a benzothieno[3,2-c]quinolinyl group; or a pyrazolo[5,1-a]isoquinolinyl group unsubstituted or substituted with an aryl group, and R104′ and R105′ are each independently an aryl group,

Z12 and Z13 are the same as or different from each other, and each independently a halogen group; a cyano group; a methyl group; a pyrimidine group unsubstituted or substituted with an aryl group; a triazine group unsubstituted or substituted with an aryl group; or a carbazole group,

and

R104 and R105 are each independently a phenyl group.

3 . The organic light emitting device of claim 1 , wherein Chemical Formula 1 is represented by any one of the following compounds:

4 . The organic light emitting device of claim 1 , wherein the organic material layer includes the electron transfer layer, and the electron transfer layer includes one or more types of the heterocyclic compound.

5 . The organic light emitting device of claim 1 , wherein the organic material layer includes the hole blocking layer, and the hole blocking layer includes one or more types of the heterocyclic compound.

6 . The organic light emitting device of claim 1 , further comprising one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, and an electron blocking layer.

7 . The organic light emitting device of claim 1 comprising:

the first electrode;

a first stack provided on the first electrode and including a first light emitting layer;

the charge generation layer provided on the first stack;

a second stack provided on the charge generation layer and including a second light emitting layer; and

the second electrode provided on the second stack, and

wherein the charge generation layer includes the heterocyclic compound.

8 . The organic light emitting device of claim 7 , wherein the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes the heterocyclic compound.