IP Library Granted Patent US 11,056,660
Granted Patent B2
US 11,056,660 · App. 15/314,922 · Granted Jul 6, 2021

Organic optoelectronic component and method for producing the same

Inventors: Silke Scharner (Regensburg, DE); Daniel Riedel (Regensburg, DE); Arne Fleissner (Regensburg, DE); Thomas Wehlus (Lappersdorf, DE); Nina Riegel (Tegernheim, DE); Johannes Rosenberger (Regensburg, DE)
Assignee: PICTIVA DISPLAYS INTERNATIONAL LIMITED
H01L51/441H01L51/0037H01L51/0056H01L51/0091H01L51/506H01L51/5072H01L51/5203H01L51/5206H01L51/56H01L2251/5369
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Quick Facts
Patent No.
US 11,056,660
App. No.
15/314,922
Granted
Jul 6, 2021
Kind
B2
Abstract

The invention relates to an organic optoelectronic component ( 10 ) comprising a first electrode layer ( 2 ), having a doped matrix material and metal nanowires, an organic active layer ( 3 ), which is suitable for emitting or detecting electromagnetic radiation, and a second electrode layer ( 6 ). The organic active layer ( 3 ) is directly adjacent to the first electrode layer ( 2 ). The invention further relates to a method for producing the organic optoelectronic component ( 10 ).

Claims (30)

1. Organic optoelectronic component, comprising:

a homogenous, single layer first electrode, which comprises a doped matrix material and metal nanowires wherein the matrix material is doped with a copper or bismuth compound,

an organic active layer, which is suitable for emission or detection of electromagnetic radiation, wherein the organic active layer is directly adjacent to the single layer first electrode, and

a second electrode layer.

2. Organic optoelectronic component according to claim 1 , wherein the matrix material comprises a hole injection material and/or a hole transport material.

3. Organic optoelectronic component according to claim 2 , wherein the matrix material is a hole transport material.

4. Organic optoelectronic component according to claim 2 , wherein the hole transport material contains or consists of at least one of the following materials: NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-benzidine); beta-NPB (N,N′-Bis(naphthalene-2-yl)-N,N′-bis(phenyl)-benzidine); TPD (N,N-Bis(3-methylphenyl)-N,N′-bis(phenyl)-benzidine); Spiro-TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-benzidine); Spiro-NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-spiro); DMFL-TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-dimethyl-fluorene); DMFL-NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-9,9-dimethyl-fluorene); DPFL-TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-diphenyl-fluorene); DPFL-NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-9,9-diphenyl-fluorene); Spiro-TAD (2,2′,7,7′-Tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene); 9,9-Bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene;

9,9-Bis[4-(N,N-bis-naphthalene-2-yl-amino)phenyl]-9H-fluorene; 9,9-Bis[4-(N,N′-bis-naphthalene-2-yl-N,N′-bis-phenyl-amino)-phenyl]-9H-fluorine; N,N′ bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine; 2,7-Bis[N,N-bis(9,9-spiro-bifluorene-2-yl)-amino]-9,9-spiro-bifluorene; 2,2′-Bis[N,N-bis(biphenyl-4-yl)amino]9,9-spiro-bifluorene;

2,2′-Bis(N,N-di-phenyl-amino)9,9-spiro-bifluorene; Di-[4-(N,N-ditolyl-amino)-phenyl]cyclohexan; 2,2′,7,7′-tetra(N, N-di-tolyl)amino-spiro-bifluorene; N,N,N′,N′ tetra-naphthalene-2-yl-benzidine.

5. Organic optoelectronic component according to claim 1 , wherein the copper or bismuth compound is Cu(I)pFBz (copper (I) pentafluorobenzene), Bi(III)pFBz (bismuth (III) pentafluorobenzene) or F16CuPc (hexadecafluorophtalocyanine).

6. Organic optoelectronic component according to claim 1 , wherein the organic optoelectronic component is an organic light-emitting diode.

7. Organic optoelectronic component according to claim 1 , wherein the metal nanowires are silver nanowires, aluminum nanowires or copper nanowires.

8. Organic optoelectronic component, comprising:

a homogenous, single layer first electrode, which comprises a doped matrix material and metal nanowires,

an organic active layer, which is suitable for emission or detection of electromagnetic radiation, wherein the organic active layer is directly adjacent to the single layer first electrode, and

a second electrode layer,

wherein the matrix material is a hole transport material, and the hole transport material contains or consists of at least one of the following materials:

N′PB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-benzidine); beta-NPB (N,N′-Bis(naphthalene-2-yl)-N,N′-bis(phenyl)-benzidine); TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-benzidine); Spiro-TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-benzidine);

Spiro-NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-spiro); DMFL-TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-dimethyl-fluorene); DMFL-NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-9,9-dimethyl-fluorene); DPFL-TPD (N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-diphenyl-fluorene); DPFL-NPB (N,N′-Bis(naphthalene-1-yl)-N,N′-bis(phenyl)-9,9-diphenyl-fluorene); Spiro-TAD (2,2′,7,7′-Tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene); 9,9-Bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene;

9,9-Bis[4-(N,N-bis-naphthalene-2-yl-amino)phenyl]-9H-fluorene; 9,9-Bis[4-(N,N′-bis-naphthalene-2-yl-N,N′-bis-phenyl-amino)-phenyl]-9H-fluorine; N,N′bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine; 2,7-Bis[N,N-bis(9,9-spiro-bifluorene-2-yl)-amino]-9,9-spiro-bifluorene; 2,2′-Bis[N,N-bis(biphenyl-4-yl)amino]9,9-spiro-bifluorene;

2,2′-Bis(N,N-di-phenyl-amino)9,9-spiro-bifluorene; Di-[4-(N,N-ditolyl-amino)-phenyl]cycl ohexan; 2,2′,7,7′-tetra(N,N-di-tolyl)amino-spiro-bifluorene; N,N,N′,N′ tetra-naphthalene-2-yl-benzidine,

or wherein the matrix material is an electron transport material, and the electron transport material comprises or consists of at least one of the following materials:

NET-18; 2,2′,2″-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole); 2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin (BCP); 8-Hydroxyquinolinolato-lithium, 4-(Naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole; 1,3-Bis[2-(2,2′-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]benzene; 4,7-Diphenyl-1,10-phenanthrolin (BPhen);

3-(4-Biphenyiyl)-4-phenyl-1-5-tert-butylphenyl-1,2,4-triazole; Bis(2-methyl-8-quinolinolat)-4-(phenylphenolato)aluminum; 6,6′-Bis[5-(biphenyl-4-yl)-1,3,4-oxadiazo-2-yl]-2,2′-bipyridyl; 2-phenyl-9,10-di(naphthalene-2-yl)-anthracene; 2,7-Bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]-9,9-dimethylfiuorene; 1,3-Bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene; 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthrolin; 2,9-Bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthrolin; Tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane; 1-methyl-2-(4-(naphthalene-2-yl)phenyl)-1H-imidazole[4,5-f][1,10]phenanthroline;

Phenyl-dipyrenylphosphinoxide; naphthalene-tetra carbon acid hydride or imides thereof;

perylene-tetra carbon acid di-anhydride or imides thereof; substances based upon siloles with a silacydopentadiene unit.

9. Organic optoelectronic component, comprising:

a homogenous, single layer first electrode, which comprises a doped matrix material and metal nanowires wherein the matrix material is doped with a copper or bismuth compound,

an organic active layer, which is suitable for emission or detection of electromagnetic radiation, wherein the organic active layer is directly adjacent to the single layer first electrode, wherein no charge carrier injection layer and/or charge carrier transport layer is arranged between the single layer first electrode and the organic active layer, and

a second electrode layer.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2020
From: OSRAM OLED GMBH
To: DOLYA HOLDCO 5 LIMITED
Reel/Frame 053464/0374 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 11/658.772 REPLACED 11/658.772 PROPERTY NUMBERS PREVIOUSLY RECORDED AT REEL: 053464 FRAME: 0395. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 11, 2020
From: DOLYA HOLDCO 5 LIMITED
To: PICTIVA DISPLAYS INTERNATIONAL LIMITED
Reel/Frame 053464/0395 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2017
From: SCHARNER, SILKE; RIEDEL, DANIEL; FLEISSNER, ARNE; WEHLUS, THOMAS; RIEGEL, NINA; ROSENBERGER, JOHANNES
To: OSRAM OLED GMBH
Reel/Frame 043443/0337 →